


No Time To Think Of Consequences

by Lil_ali



Category: Supernatural
Genre: Canon Divergence, Canon-Typical Violence, Castiel and Dean Winchester and Sam Winchester are Jack Kline's Parents, Closeted Dean Winchester, Confused Jack Kline, Dean Winchester Swears, Fluff, Getting Together, Hunting, Jack Kline and Claire Novak are Like Siblings, M/M, Meddling Kids, Protective Dean Winchester, Sassy Claire Novak, Slow Burn, Team Free Will 2.0 (Supernatural)
Language: English
Status: In-Progress
Published: 2020-03-18
Updated: 2021-01-08
Packaged: 2021-02-28 22:14:43
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 11
Words: 61,037
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23194567
Author URL: https://archiveofourown.org/users/Lil_ali/pseuds/Lil_ali
Summary: When Jody Mills calls the Winchesters for help on a case, it leads to Jack and Claire meeting for the first time. At first, they don't get along. Claire’s sassy and rebellious nature contradicts Jack’s quirky and innocent personality, but after Jack saves Claire’s life during a hunt, the pair form a friendship.That night, Claire brings up the obvious romantic tension between Dean and Castiel. Although reluctant at first, Jack agrees to help Claire with a scheme to get them together. After many failed attempts, will they ever succeed? Or will their meddling only pull Dean and Cas further apart?
Relationships: Castiel/Dean Winchester
Comments: 91
Kudos: 245





	1. Chapter 1

**Author's Note:**

> I decided to finally post this story after watching Jody's return in last nights episode. I figured we all needed a non-stressful, lighthearted, family story to entertain us, since most of us are in quarantine. I tried to add some drama to make it interesting, but I'm a sucker for fluff too. I was inspired to write this story because I always thought it would be cool to see Jack and Claire as a sibling duo, but sadly I don't think we'll ever see it in the show. So, this is kind of a Parent Trap style story. Also, this story is mainly from either Jack or Claire's Pov, since it's mainly about them coming up with ways to get Dean and Castiel together.
> 
> The reason I tagged this story as canon divergent is because it does not take place during a specific season. So, there shouldn't be any spoilers past season thirteen. You just need to know that Jack has his powers and he has a soul. 
> 
> This is not beta read, so any mistakes are my own. Thank you and I hope you like it!

Claire lazily dragged her fork through her pile of spaghetti noodles and tomato sauce. Jody’s home cooking was easy to miss after days of living off of nothing but greasy fast food and top ramen, but after being home for a while she found herself getting bored of it. Especially on days when Jody had to work late at the station and only had time to boil noodles and sauce.

Not that she would ever complain. Jody worked hard to give them a semblance of a normal life and it wasn’t her fault that Claire had weird eating habits. Some days her appetite was smaller than others and today was one of those days. She was robotically shoveling the empty carbohydrates into her mouth for the sake of muscle memory. So maybe she was getting bored of the domestic lifestyle or maybe she was just frustrated by the hunt she had been working on for over a week. It was the one reason she was stuck here for longer than she expected. All the attacks happened around the border of Sioux Falls and Brandon, which meant it was too close to home for her to walk away from.

After finding several articles on dead bodies found with fatal lacerations that seemed to be from an animal attack. This case in particular immediately caught her attention for reasons besides the location. Ever since her own brief stint of being a werewolf she had a personal vendetta towards ending any and all possible wolf attacks. At the very least she wanted to help any victims who may have been turned with the cure she learned from the Winchesters. 

Once the full moon cycle ended and more bodies continued to pop up, she put an axe through her werewolf theory. Eventually she turned to Jody for help, despite her pride screaming that she could do it herself. She was working on burying that part of her and opening herself up to help from others. Claire was so used to being on her own that it was still a foreign feeling that she was trying to get used to. 

Unfortunately, Jody was less helpful than Claire had hoped. She was useful when it came to making rational decisions and revealing confidential information the police kept, but her range of supernatural knowledge only extended slightly further than Claire’s. They tossed around the idea of it being a Wendigo, but the conditions weren’t right. Wendigo preferred the cold winters over the warm early October air. Also, Wendigo’s usually stayed in the forest close to their hibernation cave and one of the bodies had been found in the middle of a park next to a residential neighborhood. 

Then everything came to a halt yesterday when a hunter who had been working the same case turned up dead. He was young, in his early 30s. Jody said she’d only met him a few times, but she could tell he was a good guy. Of course that was all it took for Jody to freak out and they’ve stopped research ever since. 

Which led to Claire staring into her plate of her spaghetti only taking a few bites cause her stomach felt like shit. It was the typical feeling of hunter’s guilt. The mindset that every minute she sat here doing nothing, was another minute wasted. It meant another innocent person would die when she could be doing something.

“So, I called the Winchester’s. They think it may be demon related.” 

“What?” Claire shot her head up. She hadn’t been expecting Jody to talk and especially not about the case.

The Sheriff continued as if she hadn’t heard her, “They think the animal attacks might be some kind of rouge hellhound or maybe a string of crossroads deals.” 

“Sam and Dean aren’t coming here, right?” she asked.

“Yes, Claire. They are. Crossroad demons are way above our paygrade and the Winchesters handle this kind of thing all the time.”

“We don’t need them.” Claire rolled her eyes. “I can kill a demon without help from Mario and Luigi.” This was seriously what she gets for asking for help, adults holding her hand like she was a little kid.

“Yeah, right,” Alex scoffed. “You can barely kill a werewolf yourself, how are you going to kill a demon, let alone, a crossroads demon?” 

“I killed an angel that kicked the Winchester’s asses,” she boasted, leaving out how her mother died during the ordel. She still didn’t like thinking about that day. Worst birthday ever. You knew it was bad when her father’s killer and his friends were the only enjoyable part of that day.

“Need I remind you that a hunter more experienced than you, was killed by this demon,” Jody said sharply. “The Winchesters are non-negotiable. Besides, I thought it would be nice to see them again.” 

“Aren’t they busy with an apocalypse or something?” Alex asked sarcastically.

“I don’t know!” Jody threw down her fork in frustration. “All I know is that they insisted on coming. Not that I gave much of an argument, after what happened to that hunter, I figured we needed all the help we could get.” 

Claire rolled her eyes, but accepted her defeat. She could argue all she wanted, but she knew Jody wasn’t going to back down from this. 

The sheriff gave her a sympathetic look, “I don’t know if this makes it better or worse, but they’re bringing Castiel.” 

Claire agreed that she didn’t know if that was better or worse. On one hand, she was starting to miss the dork. The Winchesters hardly ever brought him along, especially for these so called “minor” hunts that they usually went on with Jody. On the other hand, she knew once he was here that the angel would go full on overprotective dad mode and not let Claire anywhere near the hunt. The case that she found and had been working on for over a week. As if Dean wasn’t already enough to deal with. 

“Who’s Castiel?” Patience asked; and Claire nearly rolled her eyes. She constantly forgot how new the psychic was to all of this and she did pity her a little bit. This wasn’t an easy life to get used to, but the girl had made the choice on her own to leave her perfect life for this shithole. Unlike Claire and Alex, who were given absolutely no say in the matter. 

“Castiel is Claire’s Dad,” Alex answered with a smirk. 

“He’s not my Dad,” Claire hissed. Honestly, she had no idea how to explain her complicated relationship with the fallen angel. Yes, he was a fatherly figure to her, but a part of her felt weird calling him that considering he wore the face of her dead father. 

“He sure acts like it…” Alex mumbled and Claire had to restrain herself from attacking her foster sister. Claire wasn’t exactly open about the details of her past and she wasn’t sure how much of it Alex actually knew. This place basically had a don’t ask don’t tell when it came to backstory. They could only assume that each girl had an equally tragic story that led them to Jody’s doorstep. Even the sheriff had a story that she didn’t like to talk about. 

“Girls that’s enough!” Jody said sharply. “Sam, Dean, and Cas are family. Which means they’re welcome here any time.” 

Claire rolled her eyes. She knew that this would be a losing battle from the start. When Jody had her mind set there was no chance of changing it. Especially when it came to Claire and hunting. “Is that it? Or are you going to tell me that Sam and Dean are bringing their mother along too? Why not make this a big family reunion?” 

“Actually there is something else I wanted to talk to you girls about,” Jody said, eyeing Claire nervously. 

“You’ve got to be kidding me.” Claire rolled her eyes and slouched back in her chair. 

“Claire, shut up and let Jody finish,” Alex hissed. Claire made a face back at her. She knew Alex just wanted to end this conversation so that she could go back to texting her current boyfriend. Claire wanted to argue that the relationship wouldn’t last, which meant their family and this case was more important, but she held her tongue. 

“Anyway,” Jody continued, “On the phone, Sam mentioned that they’re also bringing a boy that they’ve been taking care of. His name is Jack and from what I’ve heard he’s been through a lot, so be nice.”

“We’ve all been through a lot.” Claire scoffed. 

“Great, then you should be able to relate.” Jody threw back. Living with three young girls definitely made Jody more snarky and she was always quick to throw back a remark. “He acts a little… weird, so just try to go with it. He doesn’t hang out with kids his own age very often.”

“Don’t worry Jody we’ll be nice. At least, Patience and I will be,” Alex said, giving Claire a pointed look. 

“What makes this kid so special? Don’t the Winchesters usually drop wayward kids off here. We better watch out, they might be planning on leaving him here forever.” Claire knew she was being difficult, but she was still upset about Jody calling back up. 

“Let’s just say he stays with the Winchesters for… safety reasons.” The sheriff shrugged before turning on Claire, “And if I remember correctly, they would have gladly taken you in, but you wanted to be on your own.” 

Claire sighed in defeat. She knew Jody was right and she was only fighting to be petty. No matter how much she loved the dorks, living with the Winchester’s would be a nightmare. Jody and Alex were bad enough, but having Castiel constantly over her shoulder with his dumb puppy dog eyes would be worse. The corny Dad jokes and bottled up emotions would make her feel like she was suffocating. 

“Yeah, okay I’ll be nice,” Claire gave in, “I mean we’re all a little weird and have baggage. What can go wrong?”

_______________

Jack lifted his head from where it was leaning against the window as he felt the Impala roll to a stop. He stretched out the ache in his neck from the uncomfortable position he’d been in for the past hour. By now he’d been on many long and boring road trips with the Winchester’s, this one being far from the worst; and he still had not found a comfortable way to rest in a car. He asked Sam for advice, but all he enclosed was that the last good sleep he had in a car was when he was five. He warned that, “It never gets better, you just get more tired.” Jack was starting to see his point.

Jack looked out the window at the little neighborhood in Sioux Falls, South Dakota. He was feeling eager to get out of the car and properly stretch his legs, but he was less eager about what lay inside. 

“Are you sure this isn’t overkill?” he heard Sam ask Dean. “I mean, I know it’s a demon, but we usually only bring Cas and Jack for the big boss fights.” 

Dean shrugged. “We’ve brought them along for less and it’s not like they have anything better to do. Besides, Cas wanted to visit Claire and I think it’s time for Jack to meet Jody and the girls.” Jack always found it odd when Sam and Dean would talk about him as if he couldn’t hear what they were saying. He guessed that it was because Castiel and him never talked too much during these trips. Conversations were usually led by Sam or Dean.

“Who’s Jody again?” Jack asked from the backseat. All they told him was that she was a good friend and the sheriff of Sioux Falls. Which didn’t make sense to him because Sam and Dean usually didn’t get along with law enforcement. 

“Well Jack, Sheriff Jody Mills is a hunter and her place has become sort of a shelter for young girls whose lives have been affected by the supernatural.” Sam explained, “We’ve known her for years and she’s helped us out a lot. She’s a good friend.”

“Actually, she’s family,” Dean added. “Which means you better be on your best behavior..” 

Jack nodded before asking his next question, “And, who are ‘the girls’?”

“There’s Patience, she’s a psychic; there’s Alex, she was raised by vampires; and there’s Claire, she -“ Dean interrupted his brother.

“Claire is the one you really need to impress cause she’s kinda like a daughter to Cas.” 

Jack turned to Castiel, “Does that make her my sister?” 

“Uh… kind of,” Castiel said awkwardly, “but try not to call her that. She may react poorly.” Jack nodded. 

As they stepped out of the car, Jack got the chance to take a closer look at the house. It seemed to be located in an average neighborhood and the houses seemed to be fairly old. Jody’s house appeared to be one story, but covered a decent amount of land. The tall weeds and the white chipping paint showed a lack of maintenance that Jack could hardly blame the sheriff for. Being a hunter, cop, and single mom left little time for house work. 

The woman who answered the door had short brown hair and a kind face. Jack noticed the hard look in her eye when she first stuck her head out, but it slowly melted away once she saw who was on her doorstep. Jack could already tell that he would like her. 

He caught the warm motherly look she gave Sam and Dean before pulling them in for a hug. She even gave Castiel a one armed squeeze before noticing the nephilim. 

“You must be Jack,” she greeted with a welcoming smile. 

“Yes,” Jack returned the smile. Then remembering what Dean said about manners he added, “and you must be Ms. Mills.” He reached out for a handshake, which she returned. 

“Please, just call me Jody.” She gave him a warm smile. “Hope you boys are hungry, I cooked enough food to feed an army.” 

“Jody you're a saint,” Dean said with an excited look on his face, “I’m starving.”

“Really? You're starving,” Sam scoffed. “Says the guy who didn’t let us stop for six hours.”

“I wanted to get a head start on traffic. It’s not my fault you didn’t say anything.” 

“Actually, I do recall both Sam and Jack saying they were hungry and you telling them to ‘shut their pie holes’.” Castiel pointed out.

“The point is, we really appreciate this Jody.” Sam said quickly to avoid starting an argument between Dean and Cas. “The poor kid hasn’t eaten a home cooked meal in his life.” 

“It’s true,” Jack sighed. “We’ve been living off of Poptarts and Biggerson’s for the past week.” 

“That’s not true!” Dean argued. “I went to the store a few days ago.”

“Yeah, except, all you bought was beer and that box of Poptarts,” Sam corrected. 

The sound of Jody laughing cut off the brother’s argument, “Sorry don’t mind me, it’s just strange hearing you boys having domestic arguments.” Then her face turned soft, “Bobby would’ve been so proud of you.” 

“Thanks Jody.”

“Are you guys done yet?” he heard a voice say. “So we can actually talk about the case.” A girl walked into the room with long wavy blonde hair that brushed over her red flannel shirt. She was wearing a lot of eyeliner and an old shirt from a band Jack never heard of. 

“Hey kiddo, I see you’re still little miss sunshine.” Dean said sarcastically. 

“Oh, Dean is that you? I could’ve sworn you were Clint Eastwood,” she threw back. 

“Why? Cause I’m a total badass.”

“No, because you’re old.” 

“Alright. That’s enough Claire.” Jody said, trying to break up the argument. 

“No, she’s right. We should talk about the case.” Sam quickly pulled his tablet from his bag. He ignored Dean, who muttered “nerd”, as he pulled up his notes page that he had been typing during the car ride. “So, hellhounds usually only attack people who made a demon deal when their time is up. So, it’s unusual for this many attacks to happen in the same area and this close together. It’s also odd that a hunter was attacked, especially since he was working the same case which means there’s no way he could’ve made a deal.

“Now, the last time we worked a rogue hellhound case, it was going after a girl who struck it with an axe after it attacked her boyfriend. So, it is possible that he may have been protecting someone, got a hit in, and the hellhound was feeling vengeful.”

“Except, there was no other body found with him and there were no witnesses,” Dean chimed in.

“Right. So maybe there was a demon working with them? Maybe they wanted to clean up their tracks before skipping town. If that’s the case then it may be nearly impossible to know when, where, or if it’ll strike again,” Sam finished with a sigh. 

“So, that’s it? We’re just going to sit back and do nothing?” said Claire, clearly annoyed by the Winchesters.

“Relax. Sam said it was ‘nearly’ impossible, but not impossible. We clearly have enough manpower, but we just need to do a little groundwork first. Tonight we settle in and we’ll start first thing tomorrow morning,” Dean said, clapping his hands. 

“We’ve done nothing the past few days. It’s only a matter of time before another body shows up. I would have expected more from the famous Sam and Dean Winchester. Don’t you have demon connections or something?” Claire asked, desperate to take action.

“Yeah, we used to have the king of hell on our side, which would have made this case a lot easier, but with Crowley gone, we got nothing.” Dean sighed.

“I wish I got to meet Crowley.” Jack voiced the first thing that came to his mind. The Winchesters and Castiel always spoke highly of the demon, but he had died on the day Jack was born. Rowena was his mother, and Jack liked the witch, so he assumed he would have liked Crowley as well. 

“Crowley was something else, that’s for sure. He wasn’t your dad’s biggest fan, but we would’ve turned him around to you eventually,” Dean smiled at him. 

Claire threw her hands up in the air in annoyance. “Great. So, we have nothing-”

“Claire,” Jody interrupted with a sharp tone in her voice that turned back to sweet with her next sentence. “Why don’t you introduce Jack to Alex and Patience? I’ll call you when dinner’s ready.”

“Why? So, the grown ups can talk?” she scoffed.

“Yes!” Jody snapped back. She let out a breath of air and collected herself. “Look, I promise that there will be no case talk while you're gone.” 

Claire held Jody’s gaze for a moment before making up her mind. “Fine.” Then she turned to Jack giving him a once over before gesturing with her hand, “Come on.”

Jack felt unsure about what to make of Claire’s rough personality and suddenly felt nervous to find out what Alex and Patience were like. He hesitated and looked nervously at Sam, Dean, and Cas. The angel gave him an encouraging nod. While Sam said, “Go on Jack. You need to socialize with people your age...ish.” 

“Yeah kid, your social skills kinda suck and I entirely blame that on Cas,” Dean quipped, ignoring the glare Castiel was giving him. Jack moved to follow Claire, but Dean stopped him with a hand on his shoulder. He leaned down and spoke in a low voice so only Jack could hear. “Look, I know everyone here is a hunter and all, but try not to mention the whole son of Lucifer/nephilim thing. It doesn’t go well in most circles.”

Jack nodded in agreement before following Claire. He understood where Dean was coming from, but he didn’t like lying. It was not a good base to form new friendships and it always left him with a weird feeling in his stomach. Still, life with the Winchesters seemed to involve constantly lying and it was starting to become second nature. It made him feel bad regardless.

_____________

As soon as Jack and Claire were out of the room, Jody turned to them with her arms crossed. “Alright, so what’s his story? Don’t tell me there isn’t one because I know there is. I gave you a break on the phone, but you gotta fill me in.”

“Nothing gets past you, Jody,” Dean smiled before looking at his brother, unsure of where to begin. When Sam just gave him a shrug he decided to jump straight in. “He’s a nephilim. Which means he’s half angel, half human. Except, get this, his father is Lucifer.” Sam gave him an eye roll and decided to speak up when he saw Jody’s shocked expression.

“B-but, like Dean said, his mother was half human and she was an amazing person and Jack has shown no signs of being anything like Lucifer. He is good. I swear, we wouldn’t have taken him in unless we were absolutely certain.”

“How did you guys end up with him anyway?” The sheriff looked like she was still trying to process all of the information she was just given. 

“Before he was born, his mother Kelly, entrusted me with the role of guardianship. However, when he was born I was...uh...indisposed, so Sam and Dean took care of him. We’ve all sort of been watching him ever since.” Castiel explained. “But, it’s more than that, heaven and hell are constantly after him for his powers. He needs our protection.”

“Wait,” Jody held a hand, “you said you’ve been watching him since he’s been born, but Jack looks around twenty. How have I not known about this?” 

“See that’s the thing about nephilim,” Dean smirked. “He may look twenty, but he’s actually two.” 

“Wow,” Jody exclaimed with a surprised look on her face. “Okay. So, he’s been with you guys for his entire life. That explains a lot.” 

“That’s kinda why we warned you ahead of time. We were afraid you would be weirded out by the fact he has zero social skills and only understands references before 1989. No thanks to Dean.” Sam said the last remark while giving his brother a pointed look. 

“What else does he need to know?” Dean shrugged. “Everything after that is crap.” 

“You know you can’t shelter him forever,” Jody said, ignoring Dean’s comment. “I know you boys tend to be a bit overprotective. Which is fine when it comes to monsters, but one day he is going to have to figure it out for himself.”

“We know Jody. His whole life has been monsters, so it’s easy to forget to teach him the “real world” stuff,” Sam explained. “Which is why we thought introducing him to you and the girls would be the best place to start.”

“At least if he slips up here, he won’t get arrested,” Dean quipped. “And believe me, that kid slips up a lot.” 

“I told the girls to be nice. I’m not worried about Patience and Alex, although Alex can be snarky, the warning was mainly for Claire.” Jody sighed just thinking back on their conversation earlier. “Also, I apologize for Claire’s attitude. She really has been getting better. I think she’s just really frustrated with this case. Typical hunter’s guilt, she just feels like she’s not doing enough.”

“No need to apologize, Jody. I think we’ve all been on the receiving end of Claire’s wrath plenty of times. Don’t worry we’ll figure this case out. Four hunters and one and a half angels should be plenty.” Dean promised.

“I could try talking to Claire, if you think it would help,” Castiel offered.

“You're welcome to try if you want. I wouldn’t worry too much about it, I’m sure it’ll blow over once we finally solve this case.”

_______________

Claire led Jack down the hallway into one of the first rooms on the right. 

“This is my room,” she explained as they stepped through the doorway. “Sorry that it’s so empty, I don’t spend that much time here.”

“I think it’s nice,” Jack said with an honest smile. “It reminds me of the rooms in the Bunker.”

Claire gave him an odd look he couldn’t decipher before continuing. “Yeah well, you can hang out here while I get the other two losers. Just-” she hesitated, “don’t touch anything.” 

Once she left the room, Jack took the opportunity to look around. She was right in saying that the room lacked a personal touch. He understood that a hunter’s life didn't require many possessions. His eyes were drawn towards the collage of pictures and newspaper clippings thumbtacked to the wall. It was a hunting strategy that he’d see Sam do many times, Claire seemed to have the technique down to the red string strewn across in crisscross patterns. Jack began reading the articles on the “animal attacks” that dated back to weeks ago. He took notice of Claire’s original sticky notes where she drew a big X through ‘werewolf’. Underneath had ‘no relation between victims’ and ‘not a full moon’ written as bullet points. 

Dean had declined to mention earlier that Sam was the only one out of the four of them to actually research the case. Sam usually did the preliminary research on cases to make sure it was legit, then he gave them an overview of it during the car ride. Jack had offered his help, but Dean waved him off while dragging him and Castiel to his “Dean-cave”, forcing them to watch the old western marathon on TV. Jack was positive he was spaced out half the film, but he tried his best to pay attention only because Cas made him promise to pretend to like it for Dean’s sake. It ended with him falling asleep, which said a lot considering he barely needed sleep. He woke up wrapped in a blanket, with Cas softly nudging him towards his bedroom.

Basically, Jack really didn’t know a lot about this case. He figured he didn’t need to since the Winchesters usually put him on research duty while they did the field work. Apparently, he looked too young to be an FBI agent and he was a “terrible actor.” Regardless, he found Claire’s notes to be fascinating and he admired the tactical organization that shone through her hard work.

He took another glance around the room. The only other object that caught his attention was the stuffed cat sitting on her bed. It stood out since Claire didn’t seem like the kind of girl that would still keep stuffed animals. It didn’t really match her personality. The only part that did was the angry expression on the cat’s face. Jack reached out to touch it when the door opened. 

“Dude, I told you not to touch anything.” Claire walked into the room with two girls behind her. One was smirking while the other one looked almost nervous.

“Sorry. I-I just,” he quickly retracted his hand. “I was wondering why he looked so angry?” 

“Because he hates Mondays,” Claire answered with a smirk. Jack felt confused because it was a Saturday evening and why would a stuffed cat hate a weekday? He didn’t get the chance to ask because a girl with long straight black hair was walking towards him.

“Your Jack right? I’m Alex and don’t worry the rest of us here are way nicer than Claire,” Alex said with a smirk while Claire rolled her eyes. 

“Claire has been… nice,” Jack said slowly, remembering what Dean told him about being nice to the blonde.

Claire scoffed, “It’s okay, you don’t have to lie. I know when I’m being a bitch, but it isn’t your fault. It’s just this stupid case has got me in a bad mood.” Jack simply nodded in response.

“I’m Patience,” the third girl held her hand out.

“It’s nice to meet you,” Jack stated, with a friendly smile. He extended his arm to accept her offer of handshake, but the moment their hands touched, the girl quickly pulled away with a gasp. “Is there something wrong?” he asked, startled by her reaction.

“Sorry… it’s nothing,” Patience mumbled taking a few steps away from him. Jack pretended not to notice the worried looks Claire and Alex exchanged. 

“So, what’s your deal anyway?” Claire asked, clearly eager to break the tension that filled the room.

“You don’t have to answer if you don’t want to,” Alex quickly added. “None of us like talking about our past.”

“I just mean, what’s up with you living with Sam and Dean?” Claire clarified.

“Um…” Jack thought about how he should reply. He knew he couldn’t tell the truth, but he didn’t want to make up a total lie. “Why not?” he shrugged trying to buy himself extra time. 

“I mean it’s not everyday the Winchester’s take a kid in; they’re not like Jody. They’re basically lone wolves outside of each other, with the exception of Castiel.” 

“I don’t know,” he said with a thoughtful look, “I guess it’s because they’re my family. They’re all I have.” 

“Wow you really have been living with them awhile if you’re already spewing the company line,” Alex laughed, but he didn’t detect any mocking from her tone. 

“I guess it hasn’t been very long, but it feels like my whole life,” Jack chose his words carefully. 

“I get it. I barely remember my life before I came to live with Jody. Mainly because I try not to think about it,” Alex said sympathetically. Jack felt bad, they seemed to think he had a tragic backstory. He supposed his story was a little unusual, but it’s not like he had a life before he lived with the Winchester’s. He had a few faint memories from being in his mother’s womb, but those were more like thoughts and feelings. 

“So, does it suck?” Claire asked with a mischievous look on her face.

“Does what suck?” Jack asked, confused.

“Living with the Winchester’s,” she replied as if it was obvious, “I mean I love them, but if I lived with them I’m pretty sure I’d murder them in their sleep.” 

“I barely even know them and I could already tell they’d be awful housemates,” Patience spoke up. She seemed to have finally lightened up since their short handshake. 

“No, it doesn’t ‘suck.’ I like living at the Bunker,” Jack said honestly. He was aware that their lifestyle was far from normal, but that didn’t mean he disliked it. 

“You know you don’t have to lie. I promise we won’t tell anyone.”

“I’m not lying.”

“Really?” Claire stood directly in front of him, arms crossed, eyebrow raised with a challenging look. “So, you aren’t forced to only ever listen to Dean’s crappy music from over thirty years ago?” 

“It’s not that bad-” Jack tried to defend. 

“What about Sam?” Claire continued, “I bet every 5 seconds he’s trying to have a heart to heart.”

“They’re...encouraging,” 

“Then there’s Castiel, always looking over your shoulder with those sad puppy dog eyes, making you feel guilty anytime you even think about going on a hunt.” Jack stayed silent realizing that he didn’t have a response to that one. He hated the way that Claire smirked at his sign of defeat. 

“Honestly living with all men in general sounds awful,” Alex spoke. “Just thinking about the smell is disgusting.” 

“They probably never do laundry. I mean, when would they have the time?” Patience added.

“Who knows? I feel like everytime I see them they’re wearing the same clothes.” Claire commented. “That Bunker is probably a total mess.” 

“Empty beer bottles, old take out containers, weapons, yeah I’m sure it’s total wasteland.” said Alex. 

“If I had to live off nothing but burgers, beer, and pie, I’d puke.” Claire said with a grossed out look.

Jack was beginning to feel annoyed. He didn’t like the way they were talking about his life and his family. He was also feeling frustrated by the speed at which they were talking. He couldn’t get a word in to defend himself and he was feeling overwhelmed. 

“Stop it!” He said suddenly, when he realized that he finally had their attention he continued. “First of all, I don’t understand why everyone is so concerned with what I eat? I eat fine. Sure I eat like that when I’m with Dean, but Sam makes me eat healthy on occasion. He also doesn’t let me eat a lot of sugar, although Castiel does when he’s not around. S-second, Dean makes sure the Bunker is super clean. One time, it was my turn to do the dishes and I forgot. Then when Dean came home from a hunt and saw the dirty dishes he got mad and told me I was ‘grounded.’ Although, I’m still not sure what that means.” He stopped talking once he realized he was rambling at this point. He felt his face heat up when he saw all three girls giving him odd looks.

“Dude, calm down.” Claire said, a little nicer. “We were just messing with you. I’ve been to the Bunker before, I know it’s like a freakin hotel on the inside.” 

“Oh.” Jack mentally slapped himself for not understanding the joke sooner.

“Hey Jody says that dinner’s ready and if you don’t come now Sam and I will probably eat it all.” Dean opened the door and peeked his head in. He looked at them oddly when he noticed the girls had crowded around Jack. “What’s going on in here?”

Claire turned to him with a mischievous smile, “We’re talking about you behind your back.” 

“All good things?” The eldest Winchester asked nervously.

“Not really,” Alex answered. 

“Jack, don’t let them corrupt you,” Dean looked directly at him in warning.

“Too late. We already did,” Claire answered him.

“Yep, he’s moving in next week,” Alex added.

“No I’m not,” Jack said quickly, already terrified of just the thought. Dean walked in and dragged Jack by the arm, moving him protectively behind him.

“Don’t worry Jack, I’ll rescue you from these monsters,” Dean sounded serious to Jack, but when he heard the sound of the girls laughing behind him, he figured he must have been joking. When they reached the hallway, Dean lowered his voice, “But seriously kid, are you okay? You looked a little spooked back there.”

“I’m fine. They’re just a bit… overwhelming.” 

Jack’s mood improved once he had food in front of him; it turns out that Jody’s pot roast was just as delicious as Sam and Dean described. It was one of the best meals he’d eaten in his entire life. His two years of eating take out and Winchester surprise paled in comparison to Jody’s cooking. The rich flavors of the meat, carrots, and potatoes left a pleasant warm feeling flowing through his body. It left him feeling so nice that he couldn’t even bother to care about the judgmental looks all four women gave as Sam, Dean, and Jack simultaneously moaned around each bite of food. He felt bad for Castiel who just watched them all eat with a fond look while taking small sips from his bottle of beer. He silently thanked his mother for the bit of humanity that allowed him to enjoy the taste of food. 

The rest of the dinner was pretty uneventful, it mainly consisted of Jody and the Winchester’s catching up. Claire had tried to talk about the case a few times, but it usually ended with someone shrugging her off and her continuing to lazily play with her food. Soon enough they were leaving to go check into a motel room. Jack thanked Jody for dinner and she promised him that she would give them plenty of leftovers once the case was finished. They left after Dean turned to Claire and promised that tomorrow they would work on the case.

_________________

“So, are you going to tell us or not?”

“What?”

Claire and Alex were in Patience’s room, staring down the timid psychic.

“We’re not dumb Patience,” Claire pushed. “We know you had a vision when you touched that kid’s hand.”

“And we want to know what you saw,” Alex finished for her.

Patience sighed. “Fine, but don’t read too far into it because it could mean anything. B-but I think there’s something weird going on with Jack.”

“What is it? What did you see?” Claire said impatiently.

“I-I saw him get stabbed,” the girl said nervously.

“He’s going to die?” Alex asked, her eyes widening. A part of Claire felt a little worried. Sure, she barely knew the boy and he was pretty weird, but she knew he meant a lot to the Winchester’s and she didn’t want him to die.

“See, that’s the weird part,” Patience continued. “There was a knife in his chest and he didn’t even react. He just looked down at it then pulled the knife out and when he looked back up, the freak was smiling. He had this smirk on his face and his eyes were… glowing. Guys, I don’t think Jack is human.”

“M-maybe he’s an angel, like Castiel,” Alex suggested. 

“What color were his eyes?” Claire asked, recalling all the information about hunting she knew. If his eyes glowed blue then that would mean he was an angel like Alex suggested, but if they were another color it would mean he was something else.

“They were like a yellow-gold, I guess.” 

Claire sighed. Her initial instinct was to go straight to the Winchester’s motel and confront Jack head on, but Jody’s voice inside her head told her to be rational. One, she didn’t know what he was and exposing him straight on could end badly. Two, Patience visions never revealed the entire story. Maybe the demon they’re hunting possessed the poor boy and that’s why his eyes glowed. In that case informing everyone of Patience’s vision would be a good idea. Three, Jack had been living with the Winchester’s for over a year, there was no way the world’s greatest hunters never realized that he was not human. If that was true, they wouldn’t have brought him here if they thought he was dangerous.

“What should we do? Are we going to tell Jody?” Alex asked.

“No, she’ll probably just say that because Sam and Dean trust him we should too,” Claire spoke up. The other two girls were clearly looking to her for leadership since she had the most experience when it came to hunting.“We don’t do anything right now. Sorry Patience, but your visions aren’t always accurate. We’ll just keep an eye on him for now and start researching creatures with gold eyes. If anyone else finds evidence that something is off with him, we tell each other then we’ll decide if it’s worth telling Jody.”

“Yeah, like that’ll be easy. His whole personality is off.” Alex quipped with an eye roll as she went back to her room.

Claire felt uneasy as she thought about the other, more worrisome possibility. That Jack could be a powerful creature that somehow managed to slip past the Bunker’s warding and Castiel’s watchful eye under the guise of an innocent young boy. It was the perfect cover for any monster that was aware of the Winchester’s willingness to help those in need. She knew that she couldn’t make any allegations until she had all of the evidence, but she would be keeping a cautious eye on him. And if he thinks he could get away with hurting her family, then he has another thing coming to him.


	2. Chapter 2

  
The four boys arrived on their doorstep early the next morning just as promised. Sam and Dean came wearing their usual fake FBI get up, which meant that today would be a long day of going over information on the case that she already knew, but of course they wanted to start from scratch. Sometimes Claire wished they could just skip to the part where they fight the monster already. 

Jack seemed to stand out in the group since he was the only one who was wearing normal clothes instead of a suit. Claire tried imagining him in one and realized that he’d probably look more like a boy on his way to Sunday mass instead of an FBI agent. She was familiar with the feeling. She also looked way too young to be a convincing agent, so she usually settled for a different cover up. Like a student reporter or a school friend of the victim. 

“Alright, here’s the game plan,” Dean announced. “Sam and Jody will go talk to the victims' families; make sure you ask if there were any signs of strange behavior a few days before their death. Cas and I will head down to the morgue and see if we can check out the most recent body, then we’ll check out the crime scene and look for any traces of sulfur. Jack and Claire, you stay here and do research. Look for anyone whose life suddenly turned around and see if there is a pattern between the victims. We’ll meet back here around one.” 

“No,” Claire said firmly with her arms crossed. “I'm not going to stay here.”

“Fine. If you don’t like it then we can drop you off at the library on the way to the morgue,” Dean said, pretending like he didn’t know what she really meant.

“I mean I don’t want to sit on my ass all day doing research. I’ve been researching this case for weeks! I want to actually do something.” 

“Look Claire,” Sam talked slowly, trying to ration with the young girl. “We know this is your case and we don’t want to make it seem like we’re trying to take over, but you know that doing research is just as important as the fighting. We just want you to go over it with Jack and hopefully a new perspective may catch something you missed.” 

“You mean you want me to babysit the rookie?” She felt a little guilty targeting the new guy, but that’s how she interpreted Sam’s words. They needed someone to stay with Jack, while they went out and did all the cool stuff. It was the only explanation, since she had been able to force herself on to the crime scene before. 

“Jack might be new, but he’s smart. He’s done it with us enough times that he knows what to look for,” Dean defended the boy, who was currently staring at his shoes like they were the most interesting thing in the world. “Just trust our process kid, we have a pretty good success rate.” 

Great. They were treating her like a little kid. That was worse than staying behind to watch Jack. It actually hurt her feelings a little. Of course this would happen just when she believed that they had made progress. When she thought that they were starting to consider her as a real hunter. It was exactly what she feared would happen. The Winchester’s stormed in and took over while pushing Claire to the side-lines. “This is exactly why I didn’t want you to call them,” she told Jody, ignoring her look of disapproval.

“Claire,” Castiel began what sounded like another one of his sad eye speeches, but Claire cut him off.

“Save it Castiel,” she said coldly. She left the room before anything else could be said. 

She felt a little bad about blowing up on Castiel of all people. She knew he had good intentions, but she’d be lying if she said she wasn’t mad at him. Last few hunts she went on with the brothers and Jody they let her be more involved in case than research duty. Castiel was the only variable that was different today. In fact, the last time she went on a hunt with the angel he made her wait in the hotel until she had to save his ass. She understood the parental responsibility he felt towards her and she thought it was sweet, but his overprotectiveness was worse than Jody’s. Especially since she barely even heard from him for the past year. An animated gif and about a hundred emoticons on her birthday and christmas hardly counted as a conversation. 

She sulked in her bedroom until she was positive Jody and the boys had left. Then she reluctantly grabbed her laptop and walked back to the living room. She found Jack sitting at the dinner table happily reading his laptop stopping every few seconds to write in a notebook. Claire rolled her eyes at the sight and sat down as far away from him as possible. Without saying a word, she opened up her laptop thankful that he seemed content with not acknowledging her presence.

If the Winchester’s wanted her to do research, then she would do research. Although she wouldn’t be researching the case. Instead, she researched creatures with glowing yellow eyes. 

She searched the internet and the few books Sam and Dean had given her for about an hour until she reached a dead end. The only humanoid supernatural being with eyes that matched Patience’s description were yellow eyed demons known as the Princes of hell. It seemed like the closest match even after they determined that in the vision, Jack had been stabbed with an angel blade. Eliminating any possibility of him being an angel. Yellow eyed demons were one of the few creatures that couldn’t be killed by them. 

That all got scrapped when she texted Patience a drawing she found of their eyes. She immediately answered emphasizing that Jack’s eyes were gold not yellow and they only shone around his iris not his entire eye. She groaned and put her forehead on the table. She decided to keep Prince of hell in the back of her mind, since it had the closest description. She figured that yellow and gold were practically the same color, despite how adamant Patience was that they were different.

She lifted her head and dramatically flopped back in her chair. “I can’t do this anymore,” she moaned.

“Don’t worry. With both of us looking I’m sure we’ll find something soon,” Jack gave her an encouraging smile that only made her more irritated. 

“No. I mean if I have to stare at this screen for another second I will actually blow my brains out.” 

“It’s a little early, but I guess we can take a break. What would you like to do?” He said politely, closing his laptop with a grin. “At home, I like to make myself a snack. Usually, a peanut butter and jelly sandwich with a glass of chocolate milk. Sometimes I make macaroni and cheese, but after the last time I can’t unless someone else is there.” 

Claire gave him a weird look. The enigma that was Jack only continued to get stranger every time he opened his mouth. The childlike innocence that shone through his eyes as he told the story almost made Claire doubt her demon theory. Of course, until she realized that playing naive was the perfect front for a demon to hide behind. 

“Well as exciting as that sounds, I have a better idea,” she said with a mischievous look. “Instead of staying here sitting on our asses doing nothing, we can scope out the motel room that belonged to the hunter that was killed.” Claire nearly laughed at the confused look on Jack’s face. He looked like he had about a hundred different questions, but the only one he could get out was “How do you know what motel he’s staying in?” 

“Wasn’t hard,” she shrugged. “He was fairly young, no enemies, and he managed to keep his record untainted since he hasn’t been hunting for that long. Which means, he doesn’t cover his tracks well and he was dumb enough to use the same fake name twice.

“Everything is digital now, so it was easy to hack into the motel’s database and read guest history. Then I just compared the guests in all the motels in Sioux Falls with the ones in the last city he stayed in until I got a match. He paid for two weeks already, so as long as the motel staff hasn’t caught on that he died, it should be free for us to break in.” 

“Cool,” Jack had an amazed grin on his face, until he started shaking his head after realizing something. “Wait - no. Are you sure they won’t be mad if we leave when we’re supposed to be doing research.” 

“We are doing research,” she pointed out. “Besides, they won’t get mad if they don’t know we left.” 

“You want to lie?” he asked with wide eyes. “I can’t… I-I don’t like to lie.” 

“Look, you don’t have to lie. Dean and the other’s aren’t coming back till 1:00 so as long as we’re back by then, they won’t even know we left,” Claire sighed. Maybe Patience was right and Jack wasn’t a demon. He certainly lacked the delinquency of one.

“Fine. As long as we’re back before they are,” Jack gave in with a sigh. Claire gave him an excited grin before turning towards the door. She was thrilled at the idea of leaving this house for the first time in days. She almost made it to the fresh outdoors, when something Jack said made her stop in her steps.

“The four Princes of hell?” She turned around to see that Jack had noticed a book she accidently left laying open on the page she last looked at. She silently cursed herself. If Jack truly was a demon she had no doubt that he would be on to her after this. It was too big of a coincidence that Claire randomly was searching for the same type of demon that he was. “You think our demon is a Prince of Hell?” She let out a breath of relief. Maybe if she went along with the false story that she was looking for this demon instead of the one sitting in front of her; maybe she could escape his suspicions. 

“Y-yeah, I mean he seems pretty powerful,” she faked being dumb. “I figured we should cover all our options.” She let out a breath of air that she didn’t know she was holding, when he nodded in agreement. 

“Good idea,” he praised. “Except, you don’t have to worry about it being a Prince of Hell.” 

Claire narrowed her eyes at him. Either he had to confess or he would make up an excuse for knowing that information. “How do you know that?” she pressed, feeling desperate to learn the truth. 

“Because we killed them all,” he said bluntly, seeming unfazed by Claire's dark stare.

“And by that you mean?” 

“I mean they’re all dead.” He said shortly, but he further explained once he saw the confused look on Claire’s face. “There are four Princes of Hell, Azazel, Ramiel, Asmodeus, and Dagon. Dean killed Azazel, Sam killed Ramiel, the archangel Gabriel killed Asmodeus, and I killed Dagon.” If Patience hadn’t already killed her theory, it was truly dead now. Although, one part of Jack's story left her in disbelief.

“You seriously killed a Prince of Hell? By yourself?” She was almost impressed and a little confused. 

“Castiel helped… sorta,” he furrowed his eyebrows as if he wasn’t sure. “But it was mainly me.” 

Every minute Claire spent with Jack made her more and more confused. He was almost as infuriating as this case. Nothing seemed to add up. She couldn’t tell if he was an angel, a demon, or something entirely different. All she knew for certain was that he wasn’t human and he was powerful. No regular human boy his age could kill a prince of hell by himself. 

The big question was whether the Winchesters were aware of it or not. If they were, she knew that they wouldn’t have brought him over unless he was trustworthy. However, if Jack really was this powerful being, then maybe it was possible for him to slip under the Winchesters radar and past the Bunkers warding. 

Then, there was his personality. His cheerful childlike exterior was beginning to get on her nerves. She was still trying to figure out whether it was all fake or if that was just the way he acted; she didn’t know which was worse. How Dean put up with it on a daily basis was beyond her. She was beginning to think she should’ve just left him at Jody’s. 

  
Hunting with Claire was… interesting. In some ways it was similar to the Winchesters… sort of. Claire’s driving, for instance, was very much like Dean. They both neglected to follow the speed limit and played their music loud enough to indicate that they had no interest in starting a conversation with their passenger. The music they listened to even sounded alike, at least it did to Jack. However when he voiced his thoughts aloud, Claire groaned and told him it wasn’t even from the same century, before blasting the music louder to prevent Jack from talking.

She was also like Dean in the way she made Jack question whether she liked him or not. Of course he knew the eldest Winchester liked him now, but in the beginning it was less clear. But Claire couldn’t be more ambiguous. He could tell that she was trying to avoid talking to him as much as possible and when he did talk she always gave him funny looks. The only time she ever cracked a smile was when she was being sarcastic or lying. And everytime he turned his back he could feel that the girl’s eyes were on him. Jack hated it.

On the ride to the motel, Castiel texted him asking how everything was going. Jack wasn’t going to answer. He was too worried that this conversation would lead to Cas finding out that they had left Jody’s. Then he realized that if he didn’t answer, the angel would assume something had happened. So he replied:

**Jack:** It’s fine. But Idk if Claire likes me.

**Castiel:** She’s been through a lot and doesn’t let her guard down easily. Just try to “kill her with kindness” and she’ll give in eventually.

**Jack** : Being nice is hard :(

**Castiel** : If it were easy, everyone would be it :)

“Who are you texting?”

He jumped when he heard Claire’s voice. He was too busy texting Castiel to notice that the car and the music stopped. “N-no one,” he said with wide eyes.

“You were texting Castiel, weren’t you?” She asked him with her eyebrows raised. He quickly shook his head. She rolled her eyes. “Dude, I saw your screen. You didn’t tell them where we are, right?” 

Jack shook his head again. Claire sighed in relief before stepping out of the car. He followed suit. 

“I know you’re oblivious, but it’s good to know you’re not that oblivious.” 

“You know that I’m perfectly capable of lying to Sam, Dean, and Cas. I just don’t like doing it,” he defended himself. Jack didn’t like how Claire questioned his intelligence. He wasn’t clueless when it came to lying, he was just the opposite. His experience with telling lies is what made him realize why he didn’t like it. It always ended badly. 

Instead of responding, Claire started looking for room 231 with Jack following close behind. Once they reached it, Claire cursed.

“Dammit. The door’s electronic, you need a card to get in. Which means we can’t pick the lock. We have to find another way inside.” She stared at the flashing green light as if it offended her. “How obvious do you think breaking the window would be?” 

Jack knew that he could easily open the door with his powers, but doing it without Claire seeing was going to be difficult, but they had to get in the room and breaking the window would draw too much attention. 

“Let me try opening it,” Jack offered.

Claire looked unsure, “Dude, did you hear what I said? It’s impossible. There’s no lock for you to pick.” 

“Let me try. Please,” Jack said, determined. “Can you keep watch?” he waited until Claire turned her back reluctantly. Jack jiggled the door handle so it would sound like he was struggling to open the door. Then he pushed the door open with ease. He managed to snap the door lock like a toothpick. 

The second the door opened Claire whipped around and stared at him in shock. Jack gave a satisfied smile back. 

“How the hell did you open that?” 

Instead of answering her question he sighed, “Look, I know you think I’m new and I don’t know what I’m doing, but I’m not useless. I know how to hunt and I think I’m good at it. Sam and Dean have taught me a lot.” 

“I’m sorry,” Claire said with a guilty look. 

Jack continued because he felt the need to clarify that he wasn’t looking for Claire’s pity or guilt. He was just trying to reach a level of understanding. “What I’m really trying to say is, I don’t think Dean paired us up because he thinks I need a babysitter. Or because we’re both young. I think he paired us up because he thinks we can learn from each other. 

“It’s pretty clear that we’re very different people with different personalities and I can tell that you don’t like me very much,” he could see Claire begin to protest but he didn’t let her. “Which is okay, not a lot of people do. All I’m asking is that you give me a chance to prove myself.” 

“You’re right. I’ve been a total bitch,” the blonde said honestly, “I really am sorry. I’ve been told that I’m a little guarded when it comes to new people.”

“To be fair, I’ve been told that I’m too trusting,” Jack smiled and held the motel door open for her. “Like I said, we can learn from each other.” 

They stepped inside and looked around the hunter’s cluttered motel room. Claire immediately made her way over to the desk filled with paper and books while Jack began searching the inside of the duffle bag lying on the bed. Underneath a rolled up wad of unwashed flannels and underwear, he found more crumpled up papers, a flask of holy water and a silver knife. He carefully smoothed out one of the papers to read the content. They were lines and lines of what seemed to be poetry. Many were crossed out and rewritten, while some were scribbled out entirely. This was clearly a failed draft of his, but Jack still took a moment to appreciate the effort that had been put onto the wrinkled page. “He was a writer,” the nephilim said aloud with a soft smile. 

“Yeah no kidding,” Claire snapped. “Besides the books, all that’s here are these dumb poems.” 

Jack immediately got an idea and started searching through the bag faster. He dug through the side pockets and a mountain of dirty socks only to find nothing. He looked under all of the pillows only to find a small handgun. Next he stuck his hand under the mattress until his hand touched a hard object. He pulled out a thick, leather back journal. He scanned through the first couple pages to confirm that it was about hunting and he flipped to the last entry. 

“Look, I found his hunting journal,” he told Claire.

“What? How?” 

“I figured that he might have a journal since he’s a writer,” Jack explained, “Sam writes in one too, just like his father did. He’s very private about it, but he says one day he might let me read it. Anyway, he keeps it under his mattress and I guess the victim did as well.” 

“Okay spill. What does it say?” Claire asked eagerly. 

“Umm,” Jack quickly skimmed the last entry. “Well, he agrees that it is a crossroad demon gone rogue. He thinks the demon promised them ten years, but only gave them ten days. Also he figured out who his next victim is. Apparently Casey Harp recently got a full ride to NYU even though she did no extracurricular activities and she only had a 3.1 GPA,” Jack decided against asking what any of that means. It was clearly something most people that look his age already knew. “Oh no.” He said after reading the next part.

“What?”

“I guess his plan was to summon the demon on the day Casey’s deal was up. He must have thought that he could take on a demon and a hellhound by himself, but obviously he couldn’t,” Jack said with a sigh. It always made him sad when he thought too hard about the victims. It made him wonder if the hunter had a family and if they would ever get a chance to read his poems. Did they even know he was a hunter? Would they ever find out what happened to him? “Here. He wrote down the crossroads that he summoned the demon,” he showed Claire the book, she knew this area better than he did.

“Yep. That’s right next to where his body was found,” Claire said from over his shoulder. “Casey Harp. I don’t remember reading her name on any of the police reports, maybe she’s still alive.”

“Which means we can still save her,” Jack added.

They quickly put everything back where they found it, at Jack’s insistence. It felt disrespectful to leave a dead man’s belongings lying around. The only thing he let Claire take was a couple of mythology books, it was best to not let the motel staff find them anyway. She offered him one, but he shook his head and explained that there were plenty of books in the Bunker’s library. He wished he could fix the lock on the door but he only knew how to break locks not fix them and magically fixing the door would be hard to explain to Claire. 

Jack felt his stomach unclench when they managed to make it back to the house before the Winchesters, Castiel, and the sheriff. They sat back at the table and opened their computers to make it look like they had actually done research. 

Dean came storming in minutes later, with Cas in tow. “Sup nerds. Guess what Cas and I found?” then without waiting for their answer he said, “We found the crossroads where all the victims have been selling their souls.” 

“The one on Bradley and Finch?” Claire asked. “We already found it. We also found out who the next victim will be.”

“Good. So did we,” Dean said shortly. 

“Technically, Sam and Jody discovered it,” Cas corrected. 

“But, who was the one who confirmed the victims by spending an hour digging up the crossroad site?” 

“I did,” Castiel shot back with a glare.

“Yeah well it was my idea,” Dean muttered with a glare of his own. 

Jack snuck a worried glance at Claire, who seemed a little put out. She always seemed like she was trying to prove herself to the Winchesters and Jody. The location and the name were the only new piece of information they found this afternoon. Learning that they found the same information without their help, probably was a big hit to Claire’s ego. Their whole afternoon seemed like a waste of time he realized. 

Once Sam and Jody got back, Jack noticed that Claire subtly slipped away to her room again. He decided that he would let her have her space. The nephilim was certain that he was the last person she would want to see right now.

  
Jack was back in the motel room seated on the edge of the bed helping Dean clean his duffle bag full of shotguns. They weren’t the best weapon for killing a hellhound, but salt-rounds always helped to stun the pitbulls. Jack enjoyed helping the eldest Winchester clean his weapons, he found the activity to be nice and methodical. It was a job where he could be helpful without worrying about messing it up. Although Dean always told him that he was too much of a perfectionist, (Dean opted for one quick swipe from his rag, while Jack tried cleaning every smudge and dirt spot), that never stopped him from taking up his offer.

“So how’d researching with Claire go? Does she still hate you?” Dean asked casually.

“I don’t think so,” Jack started slowly, “I confronted her about it and since then she’s been a lot nicer.”

“See kid, we told you she’d come around. If you can get through to the King of Hell’s mother, you can get through to anybody,” Dean recalled with a little laugh. “Did she mention how much she hates us right now? Don’t think I didn’t notice she went to her room as soon as we got back.”

“I think she’s just upset,” Jack said honestly. “She was really excited when we found a new lead, but she was disappointed when you said you already knew. I think she feels like she has to prove herself as a hunter.”

“Claire can be… difficult. Especially when it comes to hunting,” Castiel said as he walked in the room and sat down on the couch beside Dean. “She often mistakes our protectiveness for distrust.”

“We already know she’s a kickass hunter, but sometimes we get… worried,” Dean agreed.

The conversation was interrupted by Sam walking into the room and dropping a pile of glasses in front of them, “Alright. Here are five pairs of glasses that I ran through holy fire. The fifth pair is for Jack. You probably won’t need it, but since we don’t know for sure if you can see hellhounds, you should have them just in case.” 

Jack picked up a pair of dark rimmed glasses and fiddled them through his fingers. He was excited for his first hellhound hunt. Even if he wasn’t the one to kill the mutt, he still wanted to know what they looked like. Sam and Dean would probably make him wear the glasses regardless if he could see them or not. They didn’t want Jody and Claire to get suspicious if he was the only one not wearing them (besides Castiel). Still, if he could manage it, he wanted to try and get a peek without the glasses. So that he would know for future hunts. 

“Are you guys ready?” Sam asked, looking at the three men. 

“Hell yeah!” Dean said enthusiastically. “You know how much I hate these mofos.” 

“Jack?” Sam asked, turning to him. “How are you feeling? First hellhound is kind of a big deal.”

“I feel a little bit nervous, but mostly excited,” Jack replied with a grin. He always liked hunting. Not for killing monsters, but for helping people. He was proud that their work made the world a better place. Hunting was what his family did and for that reason, Jack wanted to do it too. It reassured him that he was on the path to being a good person, given the way he could have turned out. He knew his father was probably rolling in his grave knowing the lifestyle his son led and Jack was unashamed to admit that the image made him pleased.

“Don’t be nervous kid, everything will be fine,” Dean reassured. “Just remember they are like demonic dogs. Anything that would kill a demon should kill them too. Just give them one good jab by an angel blade and they’ll be down for the count. Try not to smite them right away, it’s good for you to practice without hulking out. You are only allowed to use your powers if it’s a life-or-death situation. I’d rather you be discovered than mauled to death. Capiche?” 

Jack nodded in agreement. Although he knew deep down than he’d also break that rule to save somebody else from getting mauled. Like Dean said, he would rather get caught then let someone die.

“Alright fellas, let’s roll out,” Dean announced, slinging his army green duffel bag on his shoulder. “If everything goes right, we’ll get a celebratory beer and pizza after. Until then, eat this to fuel your energy,” he tossed Jack a package of beef jerky and a Twinkie. The nephilim shrugged and opened up the sponge cake and took a big bite. 

Sam gave him a look, “Seriously? You could have at least gone for the beef jerky. A little bit of protein is better than just straight sugar.” 

Jack gave him a guilty grin with his cheeks puffed out from the creamy filling. He swallowed the bite in one big gulp and wiped his mouth with the back of his hand, leaving behind smudged streaks of white frosting. 

Dean laughed at the scene, “And who says he’s not really my kid?” Sam dramatically rolled his eyes, but couldn’t hide the fond look he gave his brother. Defeated, Sam snatched the package of beef jerky for himself, while Jack took another bite from his sugary treat as they followed Dean out the door.

The boys met Jody and Claire in front of the Harp’s residence. Jack looked out the window and noted the nice appearance of the white suburban house. It was well maintenanced and it looked better than any house in Lebanon or Jody’s neighborhood. Jack noticed that seemed to be a common thread in most cases the Winchester’s worked. 

“So what’s the plan? The usual ‘let us in, we’re the FBI, your daughter is in danger’ spiel?” Jody asked with a hint of a laugh. 

“Yeah pretty much,” Dean replied. “Our goal here is to protect the girl and wait to see if anything comes.” 

“And if it does come,” Sam continued. “Give it everything you have. I know a demon dog doesn’t sound that big of a deal, but he will stop at nothing until he kills this girl. They don’t care about anyone that’s in their way. The only way they ever truly stop is if they’re dead.” Sam handed Jody and Claire two pairs of glasses,“Here. These will allow you to see them. When a victim’s time is almost up, they can usually detect demonic presences, so Casey shouldn’t need to wear them.” Claire and Jody both put them on. Jody’s were dark rimmed and rectangular, while Claire’s were wire-rimmed and round. 

“We don’t want to overwhelm her folks, so Sam, Jody, and I will go in first. Cas, Jack, and Claire will stay out here and be the lookout. We’ll call you in once we finish explaining the situation.” 

Claire bit back a response and settled for an eye roll that Sam and Dean intentionally ignored. Jody gave her a sympathetic smile, “at least this time you’re outside with the monster.” She followed the Winchester brothers to the front door while Castiel, Jack, and Claire hung back as expected. 

“So, how does it feel to be sitting on the bench?” Claire asked Castiel teasingly. 

“You get used to it,” Castiel sighed. “It’s not so bad when you have good company to spend it with.” The angel looked at Claire and Jack warmly. 

“Sap,” she gave Cas a friendly nudge. Jack moved to the other side of Cas as they sat on the ledge of the porch. The three of them patiently waited and kept their ears open for the sound of a distant growl.


	3. Chapter 3

**Notes for the Chapter:**

> It's only been a week and I already miss Supernatural oof. Anyways, I hope everyone is doing well and I hope you enjoy this chapter!

Castiel, Jack, and Claire sat against the front porch of the house for what felt like twenty minutes. Claire sat a short distance away, scrolling through her phone absentmindedly. Castiel stood straight, scanning the area, on alert for the first hint of a growl. However, even the angel grew tired as he stared out at the dark horizon, face hardened as if he was in deep thought. 

Similar to his father, Jack stared into the distance, trying to remain attentive, looking around for the demonic dog. He gazed where the dark sky touched the top of the trees from the forest ahead. He admired how the sky had a hue of light blue indicating the direction where the sun had set hours ago. Jack’s eyes lazily drifted downwards to the green grass under his feet. There were no signs of movement in the dirt besides a rogue ant every now and then. His eyes followed the wayward ant until it crawled underneath a smooth gray rock. The rock caught his attention as he stared at its flat surface and rugged edges. 

Jack lifted his head and took a glance towards Claire, thankfully the blonde was still scrolling through her phone. He adjusted the glasses that had slid down the bridge of the nose and checked his surroundings one last time for any sign of the hellhound. Satisfied, he looked back down at the gray rock and concentrated all of his focus onto it. He subtly lifted his index finger towards the pebble. He took a deep breath and pushed a small amount of energy out of the tip of his finger at the rock. He slowly began to drag his finger towards him. He smiled when the rock followed his finger’s movement. He made the rock slide closer and closer until it tapped his shoe. Then he moved his finger in the opposite direction, making the rock follow along. He practiced rolling the rock back and forth, making it gain momentum with every flick of his fingers. 

When he felt well practiced he suddenly stopped and took a quick glance at Claire, double checking that she was still distracted by her phone. Once he was sure he turned his attention back to the rock, only this time he lifted his finger slightly upward. He compelled the rock to levitate about an inch off the ground. It took Jack a lot of focus to ensure the rock was high enough to not touch the ground, but low enough to not draw any attention. He held the rock in the air for a moment until he felt comfortable enough to move it. He started off with a similar pattern as before, making the rock fly back and forth, almost as if he was playing catch with himself. Once he felt confident with movement, he tried creating bolder patterns. With only moving his pointer finger, he created circles, figure eights, zig-zags, and star shapes. His shapes were all drawn out carefully in the grass by his floating pebble. 

“Showoff.”

Jack immediately froze up at the sound of a voice, causing the rock to stumble to the ground. He let out a breath of relief when he saw that it belonged to Castiel, who was giving him a playful smile. “Sam says it’s good practice,” he explained. “That way I can learn how to control using small amounts of my powers at a time.” 

“Good idea,” Castiel watched fondly as the nephilim slowly levitated the rock again with his finger. He floated it around in circles a few times before gently dropping it back on the grass. 

“Can you do this?” Jack asked, referring to the rock that was hovering moments ago. He knew Castiel had powers and he knew that they were not as powerful as his own, but he never knew the extent of what his father figure could do. Cas usually refrained from using his powers unless it was absolutely necessary.

“At one time I could, but now I’m not sure,” Castiel told him with a wistful look in his eye.

“Why not?” 

“Because that’s the price I have to pay for living on Earth,” the angel answered honestly. “Everytime I’m brought back to life, my grace is recharged, but it only lasts for so long. Everytime it seems to deplete faster and faster. I don’t know if it’s the angel’s doing, or God, or nature, but ever since I first rebelled from heaven my grace has never been what it once was.”

“I live on Earth too. Will that happen to me?” Jack asked, genuinely curious. He hadn’t noticed his powers becoming weaker, but how could he be certain? He never understood the true extent of his powers, maybe he wouldn’t notice if he lost a few abilities.

“No,” the angel shook his head. “You are half human. That means a part of you is connected to the Earth. You were born here, after all. Your essence is the perfect balance between heaven and Earth. On the other hand, I am pure angel, created only to serve heaven. It is unnatural for me to become as human as I have. Angels were not meant to have emotions and yet I’ve experienced every one. I’ve accepted my fate and I do not regret my decision. If I did it all over, I would choose Sam, Dean, and you over heaven every time.” 

“Hey losers,” Cas and Jack turned to look at Claire, who had finally gotten off her phone. “They’ve been in there for a long ass time. Do you think they forgot about us?”

“Based on past experience, when Sam and Dean tell people they’re in danger, it usually leads to a lot of follow up questions.” Cas shrugged.

“Maybe you should go check on them? They might need help.” Claire suggested. Castiel looked at Claire and Jack wearily. He looked like he was conflicted between staying with them and seeing what was going on inside.

“Fine. But, you two have to stay here.” Castiel said firmly. “The second you see any sign of the hellhound run inside and warn us. Do not try to fight it by yourself. You are not it’s target, so it will not come after you unless it senses that you’re a threat.”

The two adolescents nodded in agreement and the angel hastily walked through the front door. The pair stood in an awkward silence for around thirty seconds, Jack trying his hardest to look at anything that wasn’t Claire. 

“I think I left my knife in Jody’s car,” Claire said suddenly. “I’m going to go grab it. I’ll be right back.” 

Normally, Jack would shrug off Claire’s comment, without question. However, something in her eyes made him feel like she wasn’t telling the truth. “Okay. I’ll come with you,” he offered as kindly as he could. 

“No, you should stay here and keep an eye out for Clifford. I’ll be back in a minute.”

“Um… I don’t know who Clifford is, but you shouldn’t go anywhere by yourself.”

“Why? Because you don’t think I can handle it?”

“No, because it’s dangerous,” Jack took a deep breath before revealing the next part. “And I know you’re not really getting something from the car because I saw you put your knife in your pocket when we first arrived.”

“Fine, you caught me,” she relented. “I was actually going to steal Jody’s car and fight the demon myself. I know it sounds stupid, but think about it! The Winchesters are spending all this time trying to fight a hellhound that might not even come tonight. Let’s say they do catch the hellhound, then what? The demon will just get a new pet and continue to trick people into selling their souls. We have to go to the origin, if we’re going to actually put an end to this.”

“You can’t just leave! Castiel said that we have to stay here,” Jack said firmly.

“Yeah. Well I don’t have to listen to him,” Claire scoffed. “Castiel is not my father.” She put a lot of force behind the word “not.”

“He may not be yours, but he is mine,” something in what Jack said seemed to strike a chord with Claire because she quickly turned on him.

“Fine. Since you’re such a Daddy’s boy, then feel free to stay here and not do shit. I have a demon to catch,” she swiftly turned, her blonde hair flipping with her movement. Jack stood there for a second, contemplating his next move. With a sigh he did a slight jog to catch up with the girl.

“Alright. I am coming with you.”

“Why?” Claire groaned. “You clearly think this plan is stupid.”

“I never said that,” Jack corrected. “I actually think you made a good point.”

Claire abruptly stopped and turned to him, “what?”

“I said that I think you’re right. Killing the hellhound might save Casey, but it doesn’t stop anything. We will have to kill the demon at some point and the sooner we do it, the less chance he has of killing anyone else. Besides, Sam, Dean, Castiel, and Jody are skilled hunters and they don’t need us to stop one hellhound. We’re helping more people if we do this now,” Jack explained. He still didn’t like the idea of going behind the Winchester’s backs and ignoring Castiel’s request, but he couldn’t let Claire do this alone. Going solo is what got the last hunter killed after all. “Also, I thought that we were hunting buddies.”

“Excuse me?”

“Oh right,” Jack smiled before launching into his explanation. “Sam’s number one rule is that you must always hunt with a buddy. No matter your skill level. Even Castiel takes a buddy and he has powers,” Jack refrained from saying that he had powers too and even he would prefer not to go alone. 

“You’re so weird,” Claire laughed. 

“So, what’s the plan?” Jack asked.

“It’s pretty similar to the other hunter’s plan, but it works a lot better with two people. So, I’m kind of glad you’re here,” Claire explained. “It’s simple, I’ll summon the demon and keep him distracted. Then you’ll kill him from behind when he least expects it. I know, it’s not exactly foolproof, but running into situations half-cocked is my usual style of hunting.”

“That’s Dean’s prefered method too,” Jack sighed, going over the plan in his head. “I like the plan, except I think I should be the one to summon the demon.” 

“Haha nice try,” Claire said sarcastically. “Except, I already gathered the materials for the summoning and inside of the box is a picture of me not you. Which means, I get to summon the demon.”

“I can always grab one of my ID’s from inside of the Impala,” Jack suggested. “I have a bunch and none of them are real anyway.” 

“Why do you want to be the one to do it so badly?” Claire asked, looking at him suspiciously. Jack had to think of a quick response. His true answer was, that it was safer for him to be the one within the closest proximity with the demon. If something went wrong, Jack could always use his powers as a last resort, like Dean said. It wasn’t like the demon would know how to kill a nephilim anyway. Claire on the other hand, could be killed instantly by the demon without any hesitation. 

“It’s safer for it to be me because the demon can’t kill me, or at least they won’t kill me,” Jack chose his words carefully. “Just about every demon knows who I am because I live with the Winchesters. No demon would miss the opportunity to screw with them. They’ll want me alive. Demons don’t know who you are, they could kill you before I get the chance to sneak up on them. It’s better this way, trust me.”

“How can you be so sure that they won’t kill you? What if they don’t recognize you?” 

“I can’t explain it. I just know they won’t.” Jack said as vaguely as he could. “Either way the risk is lower if it’s me.” He had to remember to say “won’t” instead of “can’t”, he didn’t want to tip Claire off in any way. Worst case scenario would be her thinking that he was somehow working with the demon.

Claire thought about it for a moment before relenting, “Fine. You can do it. It doesn’t really matter anyway.” She anxiously looked back at the house, checking that no one was coming out to look for them, “But you have to be the one to figure out how to open the Impala. I only stole Jody’s keys and I do not want Dean Winchester on my ass if you break something. You have three minutes or else I’m leaving without you.”

Jack ran to the black car thankful that Claire didn’t go with him. He could easily open the car door with his powers but it would have been harder to manage with the girl looking over his shoulder. It was easier to telepathically open a car lock than the door back at the motel. He quickly opened the drivers door and searched through the center console. He was back at Claire’s side in under two minutes. 

“I just grabbed the ID that says I’m 21. Dean only made it so that they can take me to bars, but they rarely ask and most of the time I order water.” Jack neglected to mention the times when they automatically brought him water, not believing that the ID was real. 

Claire’s face looked like she wanted to say something, but she was interrupted by a growl in the distance. “Shit. It’s here,” Claire cursed. “We have to leave now.”

Jack hesitated looking back at the house, “Are you sure they don’t need help? What if something happens?” 

“Yes it’s fine! Three badass hunters plus an angel verses one hellhound; there’s no competition. Not to mention two of those hunters are the freakin’ Winchesters! Sam and Dean can fight this dog in their sleep. They don’t need us,” Claire rolled her eyes at Jack’s still hesitant face. “Jack. We need to go now. The dog is busy. This is the perfect time to attack the demon. So you’re either coming or staying.” 

Jack sighed and hopped into the truck on the passenger side. He wasn’t confident in this plan and he knew Sam, Dean and Cas were going to be pissed when they found out he left, but there was no way he was letting Claire do this alone. 

Jack was kicking dirt with the side of his shoe burying the edges of the box that was still peeking out from the ground. Claire was currently hiding in the bushes, angel blade at the ready, waiting for the demon to arrive. Once the box was covered the nephilim carefully stepped outside of their slapdash attempt at painting a devil’s trap. It definitely lacked the precision that was present in Sam’s and Jack only hoped it would be enough to trap the demon. He stuck his hands in his jacket pockets and rocked on the heel of his foot. 

“You’re the last person I expected to see here.” In the center of the devil’s trap stood a woman with pale skin and straight long dark hair wearing a long black dress. The only splash of color on her came from her smokey bright red eyes, that flashed back to dark pupils with a blink of her eyes.

“You know who I am. Good,” he let out a sigh of relief. He would really need to improvise his part of the plan if she had no clue who he was.

“Of course I know who you are Jack,” she said with false kindness. “Everyone in hell knows who you are. Your birth caused quite the disturbance.” 

“I’ve heard. I tore a hole in the universe,” he chuckled nervously. He only hoped that Claire took his statement as a figure of speech instead of fact. 

“What do you want Jack?” she suddenly said harshly.

“W-want?” he flinched.

“Well you did call me. I’m assuming you want something?” she said with an eye roll, “I mean if you wanted to kill me, you would’ve killed me already. A mesley crossroads demon like me is nothing compared to something like you. So, what is it? Do you want to make a deal?” 

“No!” he said quickly. The last thing he needed was to accidentally sell his soul to a demon. “Um… I just wanted to talk.” 

“Talk? What could you possibly want to talk about?” 

“About the fact that you have been tricking people into selling their souls and killing them before their contract is up,” he said, feeling more confident. “Did you really think you could get away with it?” 

“Ugh, that would be why you’re here,” the demon scoffed, crossing her arms. “Did you know that everyone in hell says you’re the biggest disappointment of the century?”

“Because I’m not evil?” he asked with raised eyebrows.

“Yes!” she threw her hands up in annoyance. “You were supposed to bring about the rise of hell, but no. The Winchesters got to you first. Now they’ve ruined you like they ruin everything else and Hell has no leader.” 

“So, Hell has no ruler and you think you can just run around killing people?” 

“That’s exactly what I think! There’s no rule book which means I have free reign to collect my fee whenever I feel like it. As long as I collect souls, no one cares how I do it.” She smiled at him, “Look kid, I’m not doing anything wrong. The humans make their deal, I collect, it’s the circle of life. It’s how this system works.” 

“Except you broke the system. You’re not honoring the ten year contract. The people don’t even have time to enjoy their wishes before you kill them,” Jack argued. 

“See, I found a loophole. The contract doesn’t have to be for ten years as long as I don’t disclose it. Ask Dean, the same trick was played on him years ago.” The demon slightly crouched with her hands on her knees, she gave him another sweet smile and changed her voice to a kinder tone. She acted like she was talking to a kindergartener, “See Jack, I’ve done nothing wrong. I’m just doing my job, if these humans didn’t want to die, then it’s their fault for selling their souls to a demon. So you can just erase the devil’s trap and we can all go home.” Her sing-song voice made Jack want to groan. He may be a bit naive, but he found it demeaning anytime someone tried talking to him like a normal two year old. 

“No,” he said firmly, taking out his angel blade in what he hoped was a threatening manner. “You’re still guilty. You killed that hunter and I’m pretty sure he didn’t sell his soul.” 

“Actually, I didn’t kill anyone. My hellhound did. I can’t help that Guinevere gets feisty when people try to attack her with a big knife. Getting stabbed by hunters is the worst, I’m sure you can relate. Anyways it’s not my fault that he decided to poke the bear.” She crossed her arms impatiently. Jack was beginning to feel nervous. He was running out of ways to distract her and Claire still hadn’t come out of the bushes. It would only be a matter of time before the demon would start to get suspicious. “Now that we cleared up who the real culprit is, you can free me from this trap and we never have to see each other again.”

Jack only heard half of what the demon said, because his eyes were fixed upon the blonde speck slowly creeping out of the bushes. He nearly let out a sigh of relief, until the demon in front of him suddenly noticed that he wasn’t staring at her anymore. She slowly began to follow his line of sight when he suddenly cried out, “No!” The women’s dark eyes were now back on him looking confused. “I-I can’t just let you go,” he said weakly. He saw Claire roll her eyes in his peripheral. 

“Look, I know you were sent here to keep an eye on me while your Daddies kill my hellhound, but this is all over once Guinevere is dead. That hunter will be avenged and I will leave Sioux Falls forever and set up shop somewhere else. The Winchesters were friends with Crowley, they’ll understand that this is just business,” the demon continued to plead, thankfully not noticing Claire who was inching closer while still a distance away, angel blade at the ready. 

“No,” Jack said firmly. He was feeling more confident now that Claire was almost at the edge of the devil’s trap. “Because you’re still a demon. If I let you go you’ll just get a new hellhound and pull the same trick in another town and I can’t let you do that.” The demon smiled.

“Fine. We’ll do this the hard way,” without breaking eye contact she raised a hand directly towards Claire and slowly squeezed her hand into a fist. Claire immediately stopped in her tracks, hands reaching for her throat as she made choking sounds. “Let me out or your little friend dies,” the demon sneered, eyes turning a glowing red. 

“H-how?” Jack stammered, glancing down at the devil’s trap. 

“Oh honey, I’m not an ametur,” she laughed. “I’ve dealt with hunters before and this has to be the worst trap I’ve ever seen. It’s not even a circle! It’s an oval at best. I may not be able to get out, but some of my powers were able to slip through.” She squeezed her hand tighter making Claire’s face start to turn blue. “You have ten seconds to let me go.” 

Jack quickly nodded dragging his foot through the spray painted line, ignoring Claire who was wildly shaking her head. As promised, the moment the line was broken, he heard Claire gasping for air. The demon moved out of the trap and stood directly in front of Jack. “I’m disappointed Jack,” she said sadly, “turns out you’re just as boring as everyone says-” Before she could finish her sentence, Claire hurled the angel blade through the air in the direction of the demon. The red-eyed demon swiftly caught the blade inches from her heart. “God, I hate children,” she rolled her eyes and sent the angel blade flying back towards Claire. 

Jack saw what the demon was going to do before it happened. Without thinking, Jack shoved Claire out of the way and put himself directly in the path of the knife. He heard Claire yelling “No!” behind him. His breathing hitched the moment the knife plunged through the center of his chest. It felt like a burning hole running through his abdomen. He felt the metallic taste of blood in the back of his throat and the warm drops of blood running down his stomach and soaking through his t-shirt. He grabbed the hilt of the blade with both hands and carefully pulled it out of his chest. He felt immediate relief the moment he pulled it out as his muscle tissue began stitching itself back together. The only evidence that remained was the dark red blood stain of the front of his shirt. He slowly looked back up at the demon recognizing how the world turned a soft gold meant his eyes were glowing. He couldn’t help but smile as he saw the look of fear in the eyes of the demon in front of him. 

He heard Dean’s voice ring in the back of his head, _“You are only allowed to use your powers if it’s a life-or-death situation.”_

Taking that as all the validation he needed he continued to smirk as he raised his hand towards the demon. “You shouldn’t have done that,” he said darkly as he released a burst of power from his hand.

“You shouldn’t have done that.” 

Claire watched helplessly as Patience’s dream was unfurling out before her. The boy with the sweet smile who liked PB&J sandwiches was gone and replaced by a merciless powerful being. The sadistic smile on his face as he effortlessly raised the demon in the air was unrecognizable. 

“Demon rule number one, don’t piss off a Winchester,” he said coldly as the demon convulsed mid-air, eyes rolling to the back of her head. He watched the demon suffer as he continued to speak, “Oh by the way, you were right,” he lowered his voice, “I hate being stabbed.” Jack closed his eyes and furrowed his eyebrows in concentration. Claire watched frozen as a burst of energy came out of Jack’s hand and the demon screamed before exploding into a cloud of dust. 

Claire was quick to pull out her gun and point it in his direction the moment he lowered his hand. Jack flinched at the click of Claire turning the safety off. Claire found this reaction strange considering he had just pulled an angel blade out of his chest like it was nothing. Her puny gun would probably have no effect on him. 

Jack slowly turned around with both his hands raised in surrender. The nervous look on his face hardly resembled the menacing creature that obliterated a crossroads demon. “Claire, I-I can explain.” It was like a spell had broken and Jack had turned back into the stammering boy from earlier. 

“What the hell are you?” Claire asked sharply, keeping her gun firmly pointed in his direction.

“Claire, you know that won’t hurt me,” Jack sighed, eyeing her gun.

“Yeah, but it will slow you down,” she pointed out. “Now, answer the question,” she demanded, tightening her hold on her gun. 

“I-I’m a nephilim. It means I’m half human and half angel… archangel actually.” He explained with a nervous laugh. “But I’m good. I promise I would never hurt anyone. At least, not on purpose.”

“I don’t trust angels,” she scoffed, refusing to lower her gun.

Claire stared at him for a moment, trying to decide whether to believe him or not. Part of her believed him. He did save her life after all and he could easily just kill her right now if he wanted to. Claire knew nothing about nephilim and was basically defenseless against him. There was nothing stopping him from leaving right now, so why would he comply and answer her questions? The hunter part of her wanted to stay on guard until she was certain. “Does Sam and Dean know about..?” she gestured all around his body. She knew she trusted the Winchester’s judgement, if they knew Jack was a nephilim and deemed him safe, then they were probably right. However, if Jack had been keeping this alternate persona a secret then he was probably hiding more.

“Yes!” he said quickly. “They all know. Sam, Dean, Castiel, and even Sheriff Mills know.” 

“Try again,” Claire said, still pointing her gun directly at the boy. “If they all knew then why wouldn’t they just tell me. We’re all hunters, it’s not like it would have been a big shock.” It didn’t sound like Jody to let her work alone with Jack and not let her in on this crucial bit of information. On the other hand, it sounded exactly like Jody. They’ve been keeping her away from this whole case, of course they would keep this away from her too. Regardless, she still wanted to hear Jack’s explanation.

“I didn’t want to lie, but… Dean made me. He said that people won’t react well if they knew who my father was and based on past experience he’s right.” 

“Who’s your father?” Claire asked instinctively. Then her stomach dropped when she remembered Jack referring to Castiel as his father. The more she looked at his face, she could see a slight resemblance between the two. Jack definitely had Castiel’s personality and facial expressions. The idea alone made her feel uneasy. If this was true, did that make Jack her brother? Or not, since he technically wasn’t “Jimmy Novak’s” son. Also, who did Castiel have sex with? Her first guess didn’t seem physically possible to reproduce, but who knows how angel biology worked? 

“Is your father… Castiel?” she asked nervously, anxious to hear the answer.

“No… I mean… he is but… he isn’t,” Jack said awkwardly. Claire stared at him waiting for a better explanation. “Castiel is like a father to me, really Sam and Dean are too, but especially Castiel because before my mother died she asked him to care for me. But he isn’t my biological father. My real father is Lucifer.” 

“Lucifer?” she looked at him dumbfounded. “As in the Devil? Seriously?” Jack winced, but nodded sadly. Claire pursed her mouth. “And how is that supposed to make me trust you?” 

“Because Lucifer may be my father, but he’s not my family. Sam, Dean, and Castiel are my family. They raised me, they taught me everything I know, and they care about me,” Jack said with full honesty shining through his eyes. Claire tried to wrap her mind around everything he said.

“Wait, you look like you're about twenty. Sam and Dean have only known Castiel for like ten years. There’s no way they could have raised you,” she asked the biggest question that stood out to her. At this point she lowered her gun about halfway, but still high enough that she could shoot if she needed to. 

“Actually, I’m only two years old. I guess nephilim grow up faster than humans. Or, at least, I do,” Jack shrugged. 

“Wait, so your whole Bambi, chocolate milk, ‘we’re hunting buddies’ thing isn’t just an act?” Oddly enough, it did help explain a lot of Jack’s quirks. Him being younger than he appeared explained his lack of social skills, lack of rebellion, lack of references. 

“It’s not an act… and what’s wrong with liking chocolate milk?” he asked innocently. His face scrunched up as if he was trying to decide whether or not he had been offended. 

“This is insane,” Claire laughed running a hand through her hair. “You know what? You did save my life when you could have easily let the demon kill me. The least I can do is believe your weird ass story,” she resigned putting her gun safely away. 

“Really?” Jack’s eyes lit up.

“Yes, but,” she said sharply, raising her finger as a warning, “As soon as we meet up with the others we’re getting Sam and Dean to confirm that your story is real. Also, you’re staying within my line of sight until then.”

“That’s fair,” Jack nodded quickly in agreement. The pair walked back to Jody’s truck, Claire motioning to Jack to go first. 

**Notes for the Chapter:**

> *Supernatural Season 15 Spoiler*: The timeline of this story in accordance with the show is kind of vague, it can be assumed that its season 14ish. To clarify, it takes place before Rowena becomes the Queen of Hell, so she is still a witch in this story and hell doesn't have a leader.


	4. Chapter 4

The walk back to Jody’s car was long and awkward. Instead of walking next to Jack, Claire walked directly behind him, eyes firmly staring at the back of his head in case he tried to pull anything. She decided that she mostly trusted the boy. He hadn’t given her any reason not to, besides the whole nephilim thing. The look in his eyes as he told his story made Claire believe that he was telling the truth. Regardless if he was or not, she couldn't help but remain cautious. A lifetime of getting screwed over will do that to a person.

Part of her was grateful for the silence, Jack’s story was a lot to take in and she was still trying to absorb it all. Mainly the part about him being the devil’s son. His personality didn’t reflect that at all. If she hadn’t just witnessed him turn a demon into dust then she would have accused him of lying. It wasn’t until he explained that he had been raised by Castiel that his quirks suddenly made sense. 

Then she thought back on all of the interactions she saw between Jack and the Winchesters. They didn’t treat him like the powerful son of an archangel, they treated him more like a normal kid. Jack could have easily killed the hellhound by himself, but instead they gave him a knife and told him to be careful. He could be used as a great asset on the field, but instead they gave him a notebook and told him to stay back with Claire. And Jack just sat back and accepted it with a smile on his face. Too afraid to lie to his family when he could probably erase their memory of finding out. When the sight of Jody’s car came into view she reached out and gently tapped his arm prompting him to turn around.

“Before we go, I have another question,” Jack nodded for her to continue. “If you’re really a powerful nephilim, then how come the Winchesters stick you with me doing the easy work? I mean based on what you said, you’re probably more powerful than Castiel. Why wouldn’t they want to use that?” 

Jack shrugged, “I guess it’s the same reason they make you do it.”

“Which is?” Claire asked, genuinely curious to hear his answer. 

Jack paused for a moment. “I guess it’s because they want to protect us. I mean, I am only two years old. There is still so much about the world that I don’t know and that they need to teach me. People keep telling me that I have all these powers, but I barely know what that means and I’m still learning how to use them. I think they’re not ready for me to face the real world and they would rather keep me safe from it because they care about me. Because that’s what family does.”

“Yeah but, doesn't it get kind of annoying?” Claire asked. She understood where he was coming from, but it was odd how easily he accepted it. 

“Oh no, I find it very annoying,” Claire snorted with laughter from the honesty in his voice. “But Mary Winchester told me that it’s a parent thing and that I just have to get used to it. She said that one day they will lighten up, but it will always exist in some capacity. Just like how Dean gets overprotective of Sam even though Sam is one of the best hunters in the world.” 

“I guess you’re right,” Claire sighed. “Being overprotective is their nature... shit!” She cursed the moment she heard the creaky sound of the Impala pulling up. Claire couldn’t hold back the eyeroll she gave when Jack waved at the car with a big dorky smile on his face. 

Jody was the first one out of the car, she immediately ran up to Claire with a stressed out look on her face. “Claire! What the hell were you thinking going after the demon by yourselves? You could have been killed.”

“But we weren’t,” Claire said with a guilty smile.

“You didn’t even tell us that you were leaving! For all we knew you could have been killed or kidnapped!”

“What else were we supposed to do Jody? You guys were so focused on killing that stupid hellhound, even though killing it solves nothing as long as the demon is still alive. We knew going after the demon was more helpful than sitting around playing backup for you guys,” Claire argued. 

Jody pinched the bridge of her nose and sighed. “Yes Claire, that was a very clever idea, but if that’s what you thought we should do, then you should have brought it up earlier. That’s how being on a team works. Going off on your own, stealing my truck, and lying to us is not how a good teammate acts.” Claire clenched her jaw and looked over to where Jack was standing. While Claire was being read the riot act, Jack was practically being coddled by Sam, Dean, and Castiel. 

The moment Castiel stepped out of the car he engulfed the nephilim in a big hug and asked if he was alright. That was followed by Sam and Dean doing the same and interrogating Jack on why there was a blood stain on his shirt. Jack reassured them by lifting up his shirt to reveal clear, unharmed skin. Then the four men laughed and Dean ruffled the boy’s hair while Sam gave him a warm pat on the shoulder. 

“How is it that he gets greeted like that while I get a lecture?” Claire complained. 

Jody laughed, “Because they’re new parents and we already know that this was your idea and not his.” The sheriff leaned in, giving her a warm hug,“But believe me that I am relieved to know that you're okay.” Claire couldn’t help but smile as she hugged her back. Jody raised her voice after pulling back from the embrace, “Besides, Jack is not off the hook, right boys?” 

“She’s right,” Castiel agreed. “Jack, you know better than to run off without telling us. Going after that demon on your own was extremely dangerous.” 

“We were just trying to help,” Jack looked down at his feet. 

“We know you were and we’re not mad at you guys. We were just worried. When you leave like that, for all we know the demon could have captured you or the hellhound could have attacked you first. The least you could have done was give us a heads up,” Sam said in a calm voice. 

“Come on kid, you know better than to be stupid like that,” Dean gave Jack a gentle whack on the back of his head. 

“Look, I’m sorry that we didn’t tell you where we were going, but I didn’t think Claire’s plan was stupid,” Jack defended, rubbing where Dean had hit him. “The deaths wouldn’t have stopped unless the demon was dead. Also, it’s smarter to attack her before we killed her hellhound. If we waited until after she would have been on to us and left.” 

“You do have a good point there. In fact, I can’t believe we didn’t think about that. We were so hung up on saving the girl,” Dean admitted with a sigh. “Did you at least kill the demon?” he asked with a shrug. 

“Jack did more than kill her,” Claire scoffed. “He turned her into dust.”

“Dude, I told you to not use your powers!” Dean lightly smacked Jack’s arm. 

“You know you can say that without hitting him,” Castiel gave the hunter a look.

“You said I could use them if it was a life or death situation!” Jack argued.

“I think the real question is why did nobody tell me that he had powers?” Claire asked Sam, Dean, Castiel, and Jody. “He scared the fudge outta me when he pulled a freakin’ knife out of his chest.” 

“Look we’re sorry for not telling you. We just wanted Jack to be a normal kid for once and we didn’t want him to freak you out. I mean the kid is weird enough without knowing he’s half archangel,” Dean explained, clearly not enjoying how Claire turned the conversation on them. 

“Hey!” Jack and Cas said simultaneously. 

“I would have been a lot nicer to him if I knew more than Patience’s freaky vision where he had glowing eyes,” Claire pointed out. She felt kinda bad about it too. The Winchesters brought the nephilim along for a social experience and all he got was Claire giving him a hard time for being naive. Welcome to the real world… I guess. 

“Patience had a vision?” Jody asked, looking alarmed. 

“Don’t worry it already happened,” Claire said waving it off. 

“You know what?” Dean interrupted, saving Claire from another lecture from Jody. “It’s been a long day, it’s cold out here, and I promised celebratory beer and pizza.” 

When they got back to the Sheriff's house, Claire convinced the Winchesters to take Jody out with them to get a drink and leave Jack with Claire, Alex, and Patience. She said she wanted to make up for being mean to him earlier and give him a more accurate social experience. Dean immediately agreed and told them to have fun while Castiel seemed hesitant. 

Before walking out the door the angel warned them “to be careful” and asked Claire to not “corrupt” Jack. He looked like he wanted to say more but was stopped by Dean pulling him away by the sleeve of his trench coat. “Wouldn’t dream of it!” Claire called out with a mischievous smirk before pulling the door shut and clicking the lock. 

“Come on. Let’s get Patience and Alex.” Claire told him walking in the direction of the bedrooms. “We might have to tell them about your power thing. Like I said earlier we were kinda freaked out from Patience’s vision. Don’t worry I can leave out the whole part about being the son of Satan.” 

“That’s fine. I would’ve told you guys from the beginning if Dean hadn’t stopped me. Also, thanks for being cool about that. Most people wouldn’t want to be my friend after hearing that.” Jack said sincerely. 

“Don’t mention it.” Claire smiled at him, “We all have crap we’re dealing with.” 

Jack smiled back at her, happy that he’d finally made a friend.   
  
Alex and Patience reacted to Jack’s secret surprisingly well. Claire made her explanation short and direct. “Don’t worry guys, Jack is cool. The reason he had glowing eyes in Patience’s vision is because he is a nephilim, or half human half angel; and the reason he didn’t tell us is because Dean is a dumbass who thought we’d react as if our lives weren’t just as fucked up. Anyways, he has sick angel powers and he was pretty much raised by the Winchesters. Which means he doesn’t know much outside of Dean’s crappy music and 80s movies. So it’s our job to teach him how to be a kid from this century.” 

“Cool,” Alex responded with an approving nod. 

That’s how Jack found himself sitting on the floor of Alex’s bedroom with the three girls. Currently Claire and Alex were arguing over what movie to watch. They decided that the genre should be a classic teen movie, but they couldn’t pick which one. Jack quietly listened in knowing that he didn’t have much to add since he’d never heard of any of the movies they mentioned.

“What about _Breakfast Club_? That’s a movie that everyone has to see,” Alex suggested.

“No, he’s too innocent. Besides it’s an 80s movie, Sam will show him when he’s ready,” Claire rebutled. 

“ _High School Musical_ ,” Patience suggested. “It’s a movie our generation grew up watching.” 

“You’re getting closer, but that movie isn’t edgy enough. We’re supposed to corrupt him a little bit.” Claire said ignoring Cas’ warning from earlier. 

Jack silently watched their debate while taking a bite from his slice of pineapple pizza. Dean offered to buy them pizza before they left and thankfully the elder Winchester remembered to order one with Jack’s favorite topping. Similar to Dean, Claire looked down on the flavor and called him a weirdo. Then Alex grabbed a slice from the same pie reassuring Jack that it was a good topping and that Dean and Claire simply “lacked good taste.” Jack didn’t understand why people thought it was weird. He supposed the reason he liked it was because he had a sweet tooth. 

They ended up deciding on a movie called _Mean Girls_. After watching the first thirty minutes, he already understood the reasoning behind the title and half of the jokes were going over his head. The only reason he knew they were jokes was because the three girls would burst into laughter. 

Jack actually related a lot to the main character. She also had never attended a real school and didn’t understand what was happening. Although the way the other characters were treating her made Jack feel glad he never had to go to high school. The other girls were mean to her and even when people acted nice they didn’t really mean it. It was all very confusing. 

“So, is this how high school is like?” He asked Claire after watching the scene where the popular girls asked Cady to eat lunch with them. 

“No, the people aren’t this bad. A lot of it is overdramatized,” she told him, picking up another slice of pepperoni pizza. 

“So, the students are nicer in real life?” 

Claire thought for a moment before responding with a resounding “no.” 

Once they finished their pizza, the girls began talking over the movie. Only turning their attention back to it when they quoted a line. They started sharing information about other people. Some names he was familiar with and others he wasn’t.

“Did you guys hear that Auntie Donna is dating a new guy?” Alex said excitedly. 

“What?!” Claire widened her eyes in shock. “Please don’t tell me it’s another guy named Doug.” 

“Thank goodness it’s not. His name is Earl.” 

“Ew,” Claire winced. “That sounds as bad as Doug. Donna has such a weird taste in guys.” 

“Where did you hear this?” Patience asked. 

“I read Jody’s texts when she wasn’t looking,” Alex said with a smirk. The three girls simultaneously laughed while Jack pretended to chuckle. 

“Your turn Jack,” Claire said, the other two girls turning to stare at him. “Any drama that you want to share?” 

He shook his head. The only drama in his life involved monsters and end of times situations, they seemed to be avoiding that subject for now.”

“It doesn’t have to be ‘drama’ necessarily, just interesting facts about people we know.” Alex explained to him. “I mean you live with the Winchesters right? I’m sure you have plenty of dirt on them and Castiel.” 

“Dirt?” Jack asked, confused. He wasn’t really sure what they were asking him to say.

“Yes dirt. Like… does Sam wash his hair with women’s shampoo?” Claire asked as an example.

“Um…” He thought about it. “I’m not sure. He does have his own bottle that he keeps in his room and no one else is allowed to use it.” Jack answered, not fully understanding the purpose of this game. Was the point to share useless facts about the people he lives with?

“I knew it! He totally does!” Alex fell on her side laughing. 

The girls continued to raid him with random questions about Sam, Dean, and Castiel. They ranged from really strange to personal information that not even Jack would know the answer to. 

_When everyone is sleeping does Castiel stay up all night watching the Bachelor?_

_Does Dean secretly listen to Taylor Swift?_

_Does Sam ever wear his hair in a man bun?_

Maybe. 

Yes.

I don’t know what that is. 

“Can we stop soon? I don’t think I like this game,” Jack admitted after what felt like the hundreth question. At this point he’d rather go back to watching the movie about the mean popular girls.

“Okay last question. Then we’ll stop, we promise,” Claire gave Alex a mischievous grin.

“And this one is important so you better tell the truth,” Alex added smiling back at her partner.

“Do Dean and Cas love each other?”

Jack wrinkled his nose at the odd question, “Of course they do. They’re best friends.” He answered as honestly as he could. Technically he’s never heard them say it aloud, but he was sure that it was true. They must love each other. Like how Dean loved Sam and Castiel loved Jack. Undoubtedly, there was no way they could hate each other and stand to live in the same household. 

“No dumbass,” Claire rolled her eyes. “We mean like are they in love? Like are they in a secret relationship?” 

Jack made another face, “No way. What makes you think that?” He was shocked by their question. He has known Dean and Castiel his entire life and he had never picked up on any romantic feelings between them. In fact, based on his experience Dean and Cas argued quite often, even more than Sam and Dean. Arguments between the two brothers usually ended with an insult or the pair non aggressively wrestling on the ground. Fights between Dean and Cas however, could result in one of them storming out of the room and a round of the no talking game that could last for weeks. Looking back on it, Jack was amazed that they managed to be best friends. 

“What makes you _not_ think that?” Alex snorted. “I mean they’re so obvious. They’re always staring at each other for way longer than what’s considered normal and they have no concept of personal space. Any time they sit down they’re practically on top of each other.” 

“Also, I’ve been inside of Castiel’s head,” Claire tapped her forehead with her pointer finger. “He definitely has the hots for Dean. I swear half of his thoughts were repeating Dean’s name on overdrive. I mean he literally gave up heaven to be with Dean.” 

“Huh,” Jack said, still feeling confused. “I guess… I’ve never thought about it before.” 

“We should get them together!” Patience said squeezing the throw pillow on her lap in excitement. 

“Yes!” Alex nodded. “At this point, they’re clearly not going to do it themselves, they need a little push in the right direction.”

“And we have the perfect inside man to help us,” Claire looked at the nephilim. 

“Whoa!” Jack threw his hands up in defense. “I never said that I would do it.” 

“Don’t be lame,” Alex whined, rolling her eyes at him. “This is for their own good after all.”

“B-but…” Jack stuttered, feeling attacked. “What if you guys are wrong? What if there is nothing between them? What if we only make the situation worse? Then I am going to be the one left with the consequences.” 

“We wouldn’t do anything too extreme.” Patience pleaded. 

“I have an idea,” Claire said to him gently. “I’ll ask Sam if he thinks there is anything between them and if he says yes, then will you help us? You have to trust Sam’s opinion, he knows the two of them better than anyone else.” Jack thought about it. He did trust Sam’s opinion the most, especially when it comes to his brother. 

He carefully nodded in agreement. He still didn’t think there was anything romantic between his two adopted parents and he knew that Sam’s response would be the same, but a part of Jack also wanted the girls to be right. Castiel deserved to be happy, especially after everything he had done for him, and if Dean would make him happy then Jack would do everything he could to give him that. Also, selfishly Jack always wanted to have two parents that were in a relationship. It would give him some semblance of a normal life. 

Claire’s phone dinged and she let out a snort. She turned her phone to show me the message. 

**Sam Winchester:**

Obviously. At least, they would, if Dean ever pulled his head out of his ass. 

Jack stared at the phone in surprise. He knew he could be oblivious at times, but how could he miss something that was so obvious to everyone else? He didn’t know the first thing about romance, but he thought he knew Dean and Cas. 

Claire’s phone buzzed again as another message appeared. 

**Sam Winchester:**

DON’T TELL JACK I SAID THAT

“Oops.” Claire said once she pulled her phone back. 

Why would Sam not want Claire to tell him? The thought made him feel a twinge of irritation towards the younger Winchester. He hated when they kept information from him as if he was too fragile to handle it. Sam was usually the most forthcoming with Jack and always said he deserved to know the full truth. Then here he was treating him like a baby and it caused Jack to feel a hint of betrayal. He was pulled from his thoughts by Claire speaking up.

“Does that mean you’re game,” all three girls were staring at him expectantly. 

“Okay. I’ll do it,” he answered immediately, surprising himself. Sam’s small betrayal made him feel less guilty about accepting. If the Winchesters were so willing to tell him white lies than what did it matter if Jack did the same. 

“Awesome!” Alex squealed. “Operation Parent Trap is a go!”

“Parent Trap?” Jack said, confused. 

“You’re serious?” Claire looked at him surprised. When he stared back at her blankly, she picked up the remote and paused the movie, “I know what we’re watching next.”

“The one with Lindsay Lohan right?” Patience asked.

“There’s another version?” said Claire looking alarmed. 

Watching the next movie, Jack decided that he liked it a lot better than the first. Although he did not understand what it had to do with Dean and Cas. Jack and Claire weren’t twins and he was pretty someone would notice if they switched places. 

When he voiced his opinion to Claire, she just gave him a look and said, “Don’t be so literal. We are just watching to get ideas.” 

By the time the movie ended, Dean had texted Jack that they were on their way back to Jody’s. “So, What did you want me to do?” he asked, still not entirely sure of his part in this plan. 

“Hm, I’m not sure,” Alex sighed. “We haven’t really talked about it.” 

“We’ll call you when we come up with a real plan,” Claire told him. “Until then you can stop Dean from sleeping with other people.” 

“How do I do that?” he already didn’t like where this was going. 

“I don’t know, just try your best,” Claire argued. “Just whenever you see him act flirty, make up something that will distract him.” 

Jack internally groaned. He already knew this was going to be a challenge. Dean had a naturally flirty personality, it would be impossible to distract him every time. He even flirted with the older lady that worked at the post office and Jack was pretty certain he didn’t want to sleep with her. How would he be able to differentiate between when he was being friendly and when he actually saw the person as a potential partner?

Also, how was he going to distract Dean? Jack was not a good actor and he knew that the older hunter was aware. In fact, he could usually pick out when Jack was lying. How would he be able to successfully pull off a believable performance?

“Do I really have too?” he whined. 

“Yes,” the blonde pressed. “We can’t exactly get him with Castiel if he’s sleeping with other people.” Jack sighed already knowing this would be a losing battle. 

On the drive back to the Bunker, Jack tried to come up with ways he could distract Dean, but he came up with nothing. 

“So Jack, did you have a good time at Jody’s?” Sam asked him casually. 

Jack took a moment to think about his response. He was not sure he would describe his experience as good, but he also wouldn’t call it bad. On one hand, he felt a sense of dread from what they were making him do and frustrated by his lack of understanding the people in his generation. But, he truly did like Claire, Jody, Alex, and Patience as people and he was glad that the Winchesters introduced him. He was also happy that they accepted him for who he was and that they considered him their friend. 

“It was… enlightening,” Jack gritted out the last part as he thought back to the text Sam sent Claire. He wasn’t necessarily mad at Sam, since he never actually lied to him and it wasn’t like the subject was life threatening. But he also couldn’t help but feel bitter about the fact that Sam asked Claire not to tell him specifically. He didn’t mean to give a petty response to Sam’s innocent question, it just came out naturally. 

Thankfully, Sam just gave him a funny look and turned away. Jack took a moment to look at Dean and Cas. A part of him felt guilty about potentially lying to the most important people in his life. Then he thought back to the conversation he had with Claire and held on to the thought that this was for their own good. Besides, if they were allowed to lie to him under the condition of “keeping him safe” because they “cared about him,” then why couldn’t he do the same? 

He returned to staring out the window and prayed to no one in particular that this would work out for the better.


	5. Chapter 5

**Notes for the Chapter:**

> Sorry this one took a little longer to put out. It took me a while to feeling satisfied with it. I hope everyone is doing well! Thanks for all the kudos and comments you guys are awesome!

This step was tricky because Jack wasn’t with Dean every second of the day and he rarely hooked up with anyone when he was. There was virtually nothing he could do when Dean was by himself, but he tried his best when they were together. 

The four of them went to a diner for dinner the other night. Jack immediately picked up on the flirty smiles Dean was giving their waitress and shy grin she returned. He also took note of how Castiel immediately looked away and chose to concentrate on his menu. It reminded him why he was doing this and made him feel less nervous about what he did.

Jack loudly started to cough into the crook of his elbow. He tried to make it sound as realistic as he could without actually gagging. He coughed until “Cindy” walked away with a grossed out expression. 

He definitely took Dean’s attention away from her and put it on himself. It took Jack an hour to convince Sam, Dean, and Castiel that he wasn’t dying again. He tried telling them that he just drank water too quickly but apparently his excuse wasn’t convincing.They all kept a close eye on him the rest of the night, but at least Dean didn’t try flirting with the waitress again.

The next time it happened was when Dean took Jack to get burgers for lunch. It was going well until Jack got up to go to the restroom. When he got out he saw Dean leaning against the counter with a cheeky smirk on his face as he chatted to the woman at the cash register. Jack swiftly stepped back into the bathroom before Dean noticed him to come up with a plan. He lightly splashed water on his face and used his powers to heat up the palm of his hand. He gently put it on his forehead until it felt warm. Then he looked at himself in the mirror and practiced his sick face until he thought it was convincing enough. Then he left the bathroom and dramatically stumbled towards Dean. 

“I don’t feel good,” he moaned, lightly nudging Dean’s arm to get his attention. 

Dean looked him up and down confused, “What happened?”

“I don’t know. My stomach hurts and I feel really hot,” he gripped the counter as if it was helping him stand. 

“Are you sure?” Dean asked as if he didn’t believe him.

“Feel my head,” he nodded. 

Dean put the back of his hand to Jack’s forehead and pulled his hand back like it burned him. “Shit kid, you’re burning up. I should probably take you home,” he looked back and forth between Jack and the cashier as if he was conflicted. With an eye roll and a sigh he turned back to the woman. “Look, I’m really sorry. My kid is sick and I gotta take him home…” he apologized.

“It’s okay I totally understand. I have two sons of my own and they get sick all of the time.” She smiled and touched Dean’s hand. Jack considered throwing up on the floor to get them out of here quicker, but his better judgement decided against it. 

“Thanks. He’s probably just dehydrated, you know kids,” Dean gave her a weak smile and led Jack out of the diner. 

Once they were back in the Impala, Dean turned to Jack, “Alright faker, what the hell was that about?”

“I-I wasn’t faking,” he said trying to hide how fast his heart started beating. 

Dean rolled his eyes, “Okay first off, that’s clearly water on your shirt and your forehead is abnormally hot. Second, you were fine five minutes ago. And third, you can’t get sick.”

Jack sighed. He figured he should tell the truth since Dean already figured it out. Or at least, some of the truth. “You were flirting with that waitress.”

“So? Since when did you care whether I got laid or not?”

“W-we were having a nice time and I knew that if you left with that lady then it would end. You guys are always so busy we rarely spend time together when we’re not hunting. I just didn’t want you to leave me alone.” It was partially true. The Winchesters were busy and they often left Jack by himself in the Bunker while they went on hunts. Also, the eldest Winchester probably spent time with Jack the least and that made him sad, but he understood. Besides, he kind of enjoyed staying home when no one else was there. It was nice to have time to himself especially when Sam, Dean, and Castiel were virtually the only people he ever talked to. 

“I wouldn’t have left you,” Dean said softly. “I would have taken you home and came back when her shift ended,” he added with a playful smirk. Jack didn’t mind. He was used to Dean adding a crude joke to prevent the conversation from becoming too emotional. 

“Wait, if you know I was faking, why did you go along with it?” Jack asked, after they started driving. 

“Because acting like the shittiest Dad in the world is not going to get me laid,” Dean said flatly, “and now I can’t even go back because it’ll look like I left you in your hour of need.” Jack laughed anyway knowing what he really meant by saying that. 

Jack decided that he needed a new strategy. Pretending to be sick had been successful so far but, if he did it too much people might begin to think there was something actually wrong with him. The last waitress seemed understanding once Dean told her that Jack was his son. He filed that thought away for later.

The next opportunity he had was after a hunt the four of them went to a bar. Jack gave the bartender a nervous smile when he checked the fake ID Dean made him. Everything was going well, Sam and Dean were telling them funny stories from the long road trips they went on with their dad growing up. Until, Dean stood up declaring that he was going to buy them another round and he didn’t come back. Jack didn’t think too much about it at first, but when five minutes turned to fifteen then twenty, it was becoming noticeable.

“Where’s Dean?” he asked, interrupting Sam’s story about a wendigo he hunted with Eileen. 

“Looks like he’s busy… socializing,” Sam snorted. He nodded his head to where Dean was leaning against the bar counter talking to a woman with long wavy auburn hair. They were standing unusually close together inside of what Dean would call his “personal space” and her hand was touching his arm. “So much for getting another round,” Sam rolled his eyes. 

“It’s getting late, we should go home,” Cas said stiffly. He finally broke the glare he was giving the woman with Dean and looked down at the table in front of him. 

Sam scoffed. “It’s _not_ late, but I agree we should get going. Especially if I’m driving, I’d rather get ahead of Friday night traffic.” He pulled out his wallet and tossed a couple bills on the table. “We should watch a movie when we get home. Finally we can pick a movie we actually want to see instead of rewatching _Roadhouse_ for the 100th time.” 

Jack knew that Sam was implying that Dean wouldn’t come home with them because he’d be staying with the girl. He’s seen it before. They would leave in the Impala while Dean stayed and they wouldn't see him again until late the next morning. He’d stumbled into the kitchen with a big grin on his face wearing the same wrinkled clothes from the night before and they were all conditioned to not question it.

He also knew that people thought he was naive and while that may be true in some aspects, he picked up on a lot more than people realized. So since Sam didn’t directly say that Dean was staying it wouldn’t be out of character for Jack to misinterpret that. 

“I’ll go get Dean,” he said shortly before standing up and walking over towards Dean and the woman. He briskly walked across the bar pretending like he couldn’t hear Sam cry out “Jack, no!” He firmly planted himself in front of where Dean and the girl were leaning in to kiss. 

“Hello!” he said cheerfully, causing the two adults to jump apart. 

“Sorry kid, but we don’t want to donate to Boy Scouts of America,” the girl snapped, clearly agitated by Jack’s disturbance. Meanwhile, Dean had a horrified look on his face when he saw who was standing there. 

“Jack!” he said sharply. “What do you want?” Dean also looked annoyed by his appearance but Jack feigned innocence. 

“Sam says that we’re leaving.” 

“Okay great. I left the keys back at the table,” Dean said shortly. He was still giving Jack a look that read _why are you still here_? 

“You know this kid?” the girl looked at Dean surprised. 

“Hi my name is Jack,” he stepped forward offering his hand. When she didn’t shake it he awkwardly put his hand down. “I’m Dean’s son.” 

“Really?” the woman asked, making a face. When Jack eagerly nodded she turned back to Dean. “He’s yours?” 

“I-I mean… kinda? You know… he’s not _really_ my kid,” Dean stammered. 

“I’m not? But you said I was,” Jack tried to sound hurt. He kind of was. Just last week Dean told the diner lady that he was his son and now he was denying it. He decided that Dean was “thinking with his downstairs brain” as Sam would say. 

Guilt flashed on Dean’s face, “Fine. He is my kid. I just mean I’m not his biological father. He’s… adopted. Sorta.” 

“Wow,” the girl moved slightly away from him. “So you’re just a dick that would disown his son so he can get laid?” 

“It’s not like that. We have a great relationship, right Jack? Anyway he was just leaving,” Dean looked at him expectantly. 

“Right. I was,” Jack said catching on that Dean was getting annoyed. He didn’t want Dean to be mad at him, but he also couldn’t leave him with her. “My other Dad is going to take me home. He’s standing over there. He is that guy in a trench coat.” 

“Okay, I’m done,” the girl stood up picking up her jacket. “Look Dean, you seem like a decent guy and you're attractive as hell, but I just wanted to have some fun. All of this-“ she gestured between Dean and Jack, “-seems way too complicated and I rather not get involved.” 

“Come on, it’s not what it looks like. We’re not… and he’s… it’s complicated… I can explain.” 

She gave him a sad smile, “Word of advice: next time you want to get laid, don’t bring your entire family with you. It scares off girls like me,” then she walked away.

“She seemed nice,” Jack said, trying to hold in his triumph. 

“Shut up,” Dean growled standing up and walking in the direction of Sam and Cas.

Jack had been worried that Dean would be mad at him. The hunter tried giving him the cold shoulder during the ride home, but one glare from Cas and he stayed quiet. 

When they got home Sam promised that they could still watch a movie after they all changed to comfier clothes. Jack changed to grey sweats and a light blue sweater and made his way towards the kitchen to make himself some hot chocolate. He stopped just before the doorway when he heard Sam and Dean talking inside. 

“Damn that kid has been a cockblock lately. That’s like the third time I tried hooking up with a girl and he interrupted. You don’t think he’s doing it on purpose?” he heard Dean ask, sounding irritated. Jack held his breath. If Dean was already onto him before their plan even began then he was screwed. How was he going to follow through with the rest of the plan if Dean already had an eye on him? 

“No way,” he heard Sam laugh. “I mean this is Jack we’re talking about, he probably just misread the situation. That's definitely what happened today at the bar. Besides, why would Jack care about your sex life?”

“No clue. Do you think I should explain it to him? That way next time he’ll know?” Jack really hoped that didn’t happen. If Dean did that he’ll be all out of excuses, not to mention the sheer amount of embarrassment that conversation would make. 

“No way dude. Cas would have your ass if he heard that you ruined Jack’s innocence. Not to mention that he does not want to hear about your sex life.” 

“What the hell am I supposed to do then? Little Dean is getting restless,” Dean whined. 

“Uh… the first thing you should do is never talk about your um… ‘little Dean’ ever again,” Sam said awkwardly. “Second: you shouldn’t do anything. Jack’s a little kid and you can’t blame him for your lack of sex. He doesn’t know what he’s doing.” 

“I don’t think Jack is as oblivious as you think he is. The last time he blocked me he said it was on purpose. He said that we were having a good time and that my flirting ruined it,” Jack felt nervous again. Maybe he should have been more subtle instead of telling Dean a half truth. Sam’s long silence wasn’t helping the situation either. 

“And?” he heard Sam say after some time. “He’s right. It does ruin it.” 

“Come on, don’t give me that.” 

“Why not? Take today at the bar for instance, we would’ve stayed longer if you had come back with more beer like you said you would.” 

“Oh, I’m so sorry Samantha that you guys don’t know how to have fun without me,” Dean said sarcastically. 

“We don’t leave because we don’t know how to have fun without you. We leave because we don’t want to watch you sucking face with some random girl. It makes us all feel uncomfortable. It’s not your fault but… I’m your little brother, Jack sees you as like a father, Cas is… I don’t know. We’re your family and we don’t want to watch you doing that. It's weird dude, but that’s not the point.” Sam’s raised voice made Jack wince. He didn’t mean to start an argument between the brothers. Sam and Dean arguing was a common occurrence as long as the conversation didn’t escalate they should be over it in a few minutes.

“Yeah I don’t know how this turned on me, but it was supposed to be about the kid. What am I supposed to do? If not for my libido at least to save me from another awkward moment.” 

“Like I said there’s not much. Jack just likes spending time with you and if you get mad at him for that then you're the asshole. All you can do is wait for a time when he’s not with you. He doesn’t come on every hunt with us and you can slip out whenever you want, but until an opportunity like that comes you’re just going to have to wait.” 

“That sucks,” Dean said, sounding defeated.

“That’s parenthood.” 

Jack grinned from the other side of the wall. Then he pulled out his phone to text Claire about his success. She praised him for his cunning ability to come up with a fake excuse on the spot.

She also let him in on their next idea and it was a lot more complicated than the previous. Jack’s role specifically was going to be harder than pretending he was sick. It was Alex’s idea and it was to make Dean jealous by making it seem like Cas was texting another guy. Jack didn’t understand how making Dean upset would result in the two of them admitting their feelings, but the girls promised him that it would work.

The first thing that Jack had to do was steal Cas’ phone so that he could put in Patience’s phone number under a different name. This would be hard because Castiel was rarely on his phone and when he wasn’t he kept it in the pocket of his trenchcoat. His trenchcoat that he _never_ took off. Stealing it from his pocket while he was wearing it was out of the question. The angel would notice the second he touched his pocket. 

The only time Jack has seen him take off his coat was during movie night where they all tried to make somewhat of an effort to dress comfortably. Castiel used to keep it on until Dean convinced him that it would be better if he at least took off his coat and shoes. Even then, Cas kept his coat neatly folded next to him on the arm rest of the coach. 

The next time movie night came around Jack kept a close eye on the coat waiting for an opportunity when Cas would leave its side. That opportunity came when Dean asked Cas to help him carry the popcorn and beers while Sam tried to fix the TV. Jack subtly scooted towards the trench and dug his hand into the first pocket. What Jack didn’t anticipate was that Castiel kept a lot of stuff in his pockets. He found his wallet, three chocolate bars, a cassette tape, and a bag of honey, but he did not find his phone. Assuming it was in his other pocket Jack flipped the trenchcoat over and dug his hand into the other pocket. 

“Why are you looking through my coat?” Jack turned around to see that Dean and Cas had already come back and quickly pulled his hand out. The angel didn’t sound angry with him, only curious, giving him a bit of relief.

“Looking for your phone,” Jack admitted without further explanation. Cas raised an eyebrow like he was expecting one. “To take pictures,” he blurted out, “it’s a prank. Claire did it to me, so I thought it would be funny.” 

Accepting his reason, Castiel relaxed and sat next to him on the couch. “You know that if you wanted to take pictures all you had to do was ask. I don’t have many and I wouldn’t mind having more.” Jack quickly smiled at him and leaned back on the couch accepting his defeat. Castiel’s reaction did give him an idea. He had a good feeling that Cas might just give him the phone if he asked nicely. 

The next morning the Bunker was quiet, everyone was keeping to themselves in their own corners, and Jack figured it was a good time to try out his plan. He found Castiel lying in his bed watching cat videos on Sam’s laptop softly giggling to himself. 

“Hey Cas, can I borrow your phone? I can’t find mine,” Jack asked nicely.

“Sure,” Cas said absentmindedly holding the phone out to him, not taking his eyes off the screen. Jack quickly took the angel’s phone and left the room internally cheering at his success. He knew Castiel could be preoccupied for the next couple of hours and he wouldn’t even miss his phone, but he still got to work quickly. 

He pulled out his own phone and copied Patience’s number into Castiel’s. He created a new contact and put down the name Patrick, thinking of the movie they watched the night before. Then, he sent Claire a text from his own phone telling her to be ready in ten minutes. While he waited for her reply he started taking pictures of himself on Cas’ phone making various silly faces. This would at least give him some excuse in case Cas asked him why he kept his phone for so long. Once Claire replied he walked over to the map table where he knew Dean was sitting. 

He casually sat down near the elder Winchester and set Cas phone towards the center of the table. Then he pulled out a book and innocently pretended to be reading it. 

Jack bit his tongue as soon as he heard the phone _ding_ for the first time. He had to resist the urge to pick it up and read what it said. The girls never told him exactly what they were going to send. The phone dinged three more times before Dean started to notice. Out of his peripheral vision he saw Dean look up from the laptop he was staring at and eyed the phone oddly. 

“Damn. Kid, is that your phone that keeps going off?” Dean said after the phone made another noise. 

Jack shrugged, “No. I think that’s Cas’s phone.” 

“Huh,” Dean continued to look at the phone suspiciously. The phone went off again and Dean muttered “son of a bitch…” before picking up the phone and reading it. “Who the hell is Patrick?” 

Jack had to bite his bottom lip to stop himself from laughing, but he couldn’t hide the smile creeping onto his face. Dean noticed it and asked, “Do you know who it is?” 

Jack quickly shook his head, “I have no idea.” 

Dean hummed. His thumb was slowly scrolling through the phone like he was reading. “The only messages on here are from him. It’s probably just someone trying to reach whoever owned the phone before Cas. Either way, this Patrick guy sounds like a creep.” His fingers started typing, “Wrong number asshat,” he said along as he rapidly tapped. 

It didn’t take long before the phone beeped again. “This is Castiel’s number right?” Dean read out loud. “Who the hell does this guy think he is? No wonder Cas doesn’t answer this douche.” Jack internally debated what to say. They wanted Dean to be jealous, so he needed to convince him that this was a guy Cas was friends with and not a random number. However, he also didn’t want to get caught so he needed to act oblivious. 

“Maybe he’s a friend of Castiel’s” he suggested. 

“Nah. I’ve never heard of him.” 

“You can’t possibly know everyone he knows. Maybe he’s a friend you’ve never met before,” he said gently, fearing that Dean might redirect his anger towards him if he egged him on too much. 

“Doubt it,” Dean scoffed. “This is Cas’ personal phone not his business one. I could probably count every contact here on my fingers. He only ever talks to you, me, or Sam.”

“That’s not exactly true…” 

“Believe me, Cas doesn’t talk to anyone.”

“What do you mean I don’t talk to anyone?” 

Dean and Jack turned around to see Cas walking into the room. He was giving Dean a pointed look. 

“I… uh…” Dean looked like he was trying to come up with a response. “I-I just meant that you don’t text people very often. You know, outside of me, Sam, a-and Jack,” Cas relaxed.

“I suppose that’s true. Although I don’t know why you…” Cas paused once he noticed the phone in Dean’s hand. “Why do you have my phone?” 

Dean's face reddened and to be honest Jack didn’t feel great either. This whole situation was going downhill fast. Dean was never supposed to open the phone, Cas was never supposed to walk in, and this whole situation could be easily traced back to him. 

“Well… it was just on the table… a-and it kept going off… it could’ve been an emergency… and…. and who the hell is Patrick?!” Dean looked like he was struggling to get his words out. He was caught between shame, embarrassment, and anger. 

“Patrick?” Cas repeated, confused. “I don’t even know a… actually I do know one Patrick.” He took his phone back and read through the messages with Dean hovering closely above his shoulder. “Although this doesn’t sound like him.” 

“What? Is he a heaven buddy of yours?” Dean asked, still sounding defensive. 

“Yes, but he is not a ‘buddy’. In fact I kinda hate Patrick. I thought he died a long time ago,” Castiel informed. He was still staring at the screen in puzzlement. “I’ll tell him to stop sending me inappropriate messages.” Jack cringed. This was going terribly and he was almost glad he couldn’t read whatever Claire had been sending. 

“I got a better idea,” Dean said, stealing Castiel’s phone from him again. “I’ll block the number. That way you won’t get texts from that asshat again.” 

“Thank you,” Cas said politely, taking his back once Dean was finished. “Now back to my original question. What made you think going through my phone was okay?” the angel said sternly, staring at Dean.

The hunter rolled his eyes. “Sorry buddy, but if your cat gifs to Sam are so private then you shouldn’t leave your phone in the middle of the table for everyone to see.”

“I didn’t leave it on the table. I gave it to Jack.” Suddenly both adults were staring at him waiting for an explanation. 

“I’m sorry!” he said quickly. He felt his face turn red as he scrambled for a safe response. “I-I was going to give it back, but when I checked your room you weren’t there, so I thought that I would hold onto it.” 

Castiel stared at him for a moment. It seemed like he was trying to determine whether he was lying or not. He must have found what he was looking for because his face slowly softened. “Alright.” Him and Dean both took a seat at the table again. Jack pretended to read, but he could still feel the two pairs of eyes on him. Feeling uneasy, he quickly stood up and retreated back to his room leaving the book behind. Once there he closed the door and let out a breath that he didn’t realize he was holding. He pulled out his phone and saw a text from Claire.

**Claire Novak** :

  
HE BLOCKED IT?!

  
CALL ME NOW

Jack called her only to replay the entire story to her, Alex, and Patience who were listening in on speaker phone. They all sounded very disappointed by their failure although they didn’t blame Jack for it. 

“Was he at least a little jealous?” Alex asked, sounding desperate. 

“Maybe?” Jack said not entirely sure. “He seemed kinda angry that he didn’t know who Cas was getting messages from. He kept insisting that he knew everyone Cas was friends with.”

“Ugh,” he heard Claire groan. “He is so insecure. But we can work with that.” 

“So, new plan?” Jack asked nervously about what their next idea would be. He hoped that he was less involved in the next one. 

“Yeah, we’ll call you when we think of a new one,” Claire told him with a sigh. 

“If it could involve less lying, I would be very grateful,” Jack said hopefully.

“Yeah we’ll see,” Claire scoffed. 

After he hung up with Claire, Jack came up with a plan of his own. He decided he wouldn’t run it past Claire, since he knew she would veto it immediately. He wanted to try talking to Dean and Cas individually. To see if he could get them to indirectly admit their feelings about each other to him. It wouldn’t do much since they won’t be admitting it to each other, but Jack just wanted justification that he was doing the right thing. He’d feel awful if they interpreted the situation wrong and all their work was for nothing. 

He knew Claire wouldn’t like this plan since it didn’t involve deception and Jack wasn’t exactly known for his subtlety. In fact he wasn’t entirely sure how he’d pull this off, but he would try his best. After all, he may not know how to read social cues, but he liked to think that he knew Dean and Cas.


	6. Chapter 6

**Notes for the Chapter:**

> This chapter is a little shorter than usual, but I think it's important. I hope you enjoy it!

  
Jack decided that he would talk to Castiel first. He was closest to the angel and he was more likely to open up to him than the eldest Winchester. He just wasn’t sure how to go about it. 

Since Jack was only three years old, the Winchesters and Castiel were used to him asking weird questions. The nephilim hoped that if he screwed this up he could hide behind that cover and Cas was the most likely to be forgiving.

“Do you like Dean?” Jack blurted out late one night after Sam and Dean had gone to bed. Cas and him were drinking coffee together at the kitchen table. Jack always appreciated any time he spent alone with his father, but he liked these times the best. On days when Jack didn’t feel tired and could spend a portion of the night awake with the angel. 

They had been sitting together in a comfortable silence and he thought that this was the perfect time to talk to him. However, he hadn’t actually planned out what he wanted to say, but he didn’t want to miss this opportunity. That led him to asking the awkward question. 

“Of course I _like_ Dean.” Castiel said, giving him an incredulous look. “He’s my closest friend and I’d die for him.” That wasn’t exactly what Jack had been looking for. 

“But do you _love_ him?” he tried again. He knew the question was a little forward, but he couldn’t think of another way around it. 

“Yes, I do love him,” Castiel answered softly without hesitation. Jack felt his heart soar. “As I said I would die for him without thinking twice about it and I would follow him to the end of the earth. He is one of the most important people in my entire existence. I love him just as I love you.” Okay, that also wasn’t what he was looking for. He knew Castiel didn’t love the two of them in the exact same way. Cas loved Jack like a son and he was sure he didn’t see Dean that way. No, Cas loved Dean like a… well that’s what he was trying to figure out.

“But, you don’t love Dean the same way you love me. Right?” 

“I suppose not…” Cas trailed off looking at him oddly. “Are you trying to ask me to pick between the two of you.”

The nephilim quickly shook his head, “No. Of course not.” 

“Because if we were talking about a life threatening situation I would pick you,” Cas answered anyway. “You are still very young and you deserve to live a much longer life. Besides, I think Dean would agree with my reasoning and he would forgive me eventually. If I let you die, I don’t think either of us would be able to-”

“That’s not what I was asking,” Jack interrupted. That was far from his point and he did not like to think too hard about any of them dying.

“Then why are you asking me this?” 

Jack scrambles for an answer. “I just learned that there are different types of love. Like how the way you and I love each other is different from the way Sam and Dean love each other. I guess, I’m just trying to understand it.” It was sort of a lie. He didn’t just learn this, Dean gave him a long explanation of the subject recently. But he figured that it was a good cover. 

Castiel smiled. “I understand. I am still trying to grasp the topic myself. Feelings are still very new to me and I’m still trying to come to terms with my own. What they mean and why I feel a certain way.” That seemed rather vague to him, but he nodded for the angel to continue. “I suppose the way I feel about you is different from the way I feel about Dean and that’s different from the way I feel about Sam. Although I know that I love you all very much. The way I feel about you is similar to the way a father loves his son. I’ve watched you grow from the moment you were born and I feel an overwhelming urge to protect you from any harm. 

“The way I love Sam is like a brother. I feel a strong sense of loyalty to him and I would fight side by side with him any day. As I know that he would do the same for me. The way I feel about Dean is… well it’s rather complicated.”

“How so?” Jack pressed, feeling like he was sitting on the edge of his seat. He already was aware about everything Castiel said about him and Sam. Dean was the one he really wanted to hear him explain.

Castiel thought about it for a moment, obviously thinking about what he was going to say. “I suppose the way I feel about Dean is akin to a best friend. He is my most trusted confidant and he certainly knows the real me better than anyone else in the universe. But labeling that relationship with a term as simple as ‘best friend’ doesn’t feel right. Dean and I share a profound bond. Our destinies linked together the moment I raised him from hell. His soul was so pure and bright, yet so damaged. It was beautiful.

“Dean is what made me the person I am today. I owe him everything. I feel so much for him it’s difficult to describe in just one word.” He shook his head as if he had come out of a daze, then his look turned sadder. “But, unlike you or Sam, I doubt Dean sees me in the same light I see him. In fact, I know he doesn’t,” he laughed dryly. “That probably didn’t make any sense. I don’t think I even answered your question.” 

“I understand,” Jack told him with a soft smile. “And you answered perfectly. And Dean does feel the same way. He has too.” 

His talk with Castiel proved that the angel did indeed have feelings for Dean. He didn’t have to say it directly for Jack to see it in his eyes. It also fueled him further to make sure his plan with Claire worked. After everything, Castiel deserves to be happy and Jack would do anything to make that happen. The last part of Cas’ speech did hurt him a little because he didn’t like how lowly the angel thought of himself. Jack knew it couldn’t be true. Dean _must_ feel the same way. How could he not? Cas was the best person Jack had ever met and he knew it before he was even born. If Jack could make his mother see it, then he could make Dean see it too. 

“Even if he didn’t, I still love you,” Jack gave his father an awkward hug from across the table.

“I love you too Jack,” he heard him say softly as he returned the hug. 

After that Jack rushed to his bedroom so that he could think of what he would say to Dean. He already knew Jack couldn’t be as straightforward as he was with Castiel. Naturally Dean just wasn’t as willing to open up about his feelings. Jack was also nervous because if he slipped up then it could potentially end with Dean getting angry and Jack would prefer to avoid that at all costs. 

The next morning, Jack found Dean in the Bunker’s garage working underneath the hood of the Impala. Jack slowly walked over to him. “Hello!” He said cheerfully, he needed to make sure the hunter was in a good mood. 

“Hey kid,” Dean stood up straight. “Did you want to give me a hand?”

“Really?” Jack lit up. “You would let me help?” Dean never let Jack anywhere near him when he was working on the Impala. Dean said he wasn’t ready and that Sam had to wait 24 years before he taught him how to work on the car. 

Dean made a face. “Not exactly. This is hard work and you’re still only three. But I will let you do what I did for my Dad at three. Actually I was six, but I think you can handle it.” He dragged a stool next to the car and gestured for Jack to sit. “I sat still and handed my Dad whatever he needed.” He shoved his tool box in his lap and went back to working on the car. Jack didn’t mind that he gave him an easy job, he was happy to help out in any way he could. It also warmed his heart to hear that Dean was letting him do a task he usually did for his father. 

He stayed silent for the first thirty minutes. Trying to get the hang of figuring out what Dean needed. Jack didn’t understand any of the terms Dean was using and was merely guessing what tool it was. Anytime he handed him the wrong tool Dean would grunt, hand it back, and vaguely gestured towards the one he wanted. The beginning was spent in confusion, but once he started memorizing the names it went a lot more smoothly. Once they were in a nice rhythm, Jack decided to ask his question.

“Are you in love with anyone?” Jack asked as innocently as he could. He knew it wasn’t much better than what he asked Cas, but he didn’t have any other ideas.

“What the hell kind of question is that?” Dean said grumpily, not even looking up from the car. 

“Just answer,” he pressed, figuring it worked with Cas. 

Dean took a quick glance at him before going back to the car. “Jack, we already had this conversation a while back and I’d rather not repeat it.” 

“It’s not like that. I’m just wondering if you know what it feels like,” he said, trying a different angle. 

“Kid, if you’re having girl trouble just say so.” 

“I’m not having girl trouble.” 

Dean looked up at him. “Is it boy trouble?”

“No, it’s not about me.” 

“Cause if you are, just know that we’re okay with it,” Dean continued, ignoring what Jack said. “Sam, Cas and I will still support you if you swing the other way.” 

“That’s not what I-”

“Or you might swing both ways. That’s fine too,” Jack groaned. Dean really mastered the art of steering the conversation away from himself. He figured a lifetime of lying will do that to a person.

“I’m not talking about myself,” he said firmly. He continued before Dean could interrupt him again. “It’s just that I see people in love in movies all the time, but I’ve never actually seen it in real life. That’s why I’m asking you.”

Dean sighed. “I could tell you about me if you really want me to, but I don’t know how interesting it will be. I’m sure Sam will have a lot more to say.” 

“That’s okay, I still want to know what you have to say,” Jack encouraged.

Dean was quiet for a moment. “There've been a few times where I thought that I was in love… but I’m not so sure anymore. I look back on it and I think I was just young and naive.” 

“What about now?” Jack pushed, trying to get closer to the answer he was really looking for. 

“Now? I don’t have anything going on now - carburetor,” Dean said shortly, holding out his hand towards Jack. The nephilim had to think for a moment before he remembered what he was doing. He carefully picked up the part and placed it in his hand. Dean went back to hiding his face under the hood of the car before he continued. “The most recent experience I had was with this girl named Lisa. We were together, but that was nearly a decade ago. I think I was in love with her at the time. I was living with her and her son Ben for a while. I thought I had lost everything, Sam was in the cage with Lucifer and Cas was busy ruling heaven. She was all I had… but that relationship was destined for disaster the moment I showed up on her doorstep.” 

Dean went quiet after that and Jack felt disappointed. This conversation was not going as well as he had hoped and he knew Dean was reaching his breaking point. If he toed the line any further Dean might get angry with him, but he had to. He owed it to Castiel to try harder.

“Have you felt anything since then?” he asked gently. 

“Nothing that would work out,” Dean mumbled, not meeting Jack’s eye.

The Nephilim perked up, “That indicates that you have. Just because you don’t think it would work out doesn’t mean you aren’t in love.” 

“Actually it does,” Dean snapped. “Look Jack, you're a kid and you only know about romance from movies, but in real life it’s a lot more complicated. It isn’t enough to be ‘in love.’ If your lives are not compatible then it makes everything else impossible. Doesn’t matter how much you care about the person.” He went quiet after that and Jack didn’t comment. Dean seemed upset and he didn’t want to say anything to make it worse. “By the way, I was being general, I wasn’t talking about anyone specific. There is absolutely no one I know that I have any feelings for.”

“No one?”

“How many fucking times do I have to tell you I don’t have feelings for anybody?!” Dean flared, then pinched the bridge of his nose. “You know what Jack? You can leave, I’m almost done here anyway.” 

Not wanting to make Dean more upset, he stood up taking his cue to leave. “I’m sorry for upsetting you,” he mumbled before turning and heading for the exit. 

“Jack wait,” Dean sighed, stopping Jack as he was reaching for the handle. “I’m sorry for getting mad at you like that. I feel like an asshole. It's a sensitive subject for me, but that is not your fault.” 

“It’s fine. I’m sorry I pushed it,” he said quietly. 

“I told you that you should have asked Sam cause I knew whatever I’d say would be crappy. His speech would be better and he’d be able to say it without blowing up.” Dean gave him a half smile to show that he wasn’t mad at him. Jack wasn’t afraid of Dean anymore, but he knew the hunter still felt guilty about the time when he was. “Listen, I don’t want you to feel sorry for me because of anything you heard me say right now. I am fine. Seriously. People make it seem like you have to have this big romance in order to be happy, but I want you to know that’s not true. I am content with not having that type of relationship. 

“It’s not like I’m lonely. I have you, Sam, and Cas to annoy the crap out of me on a daily basis. You guys are all I need. If I want sex, then I go out and find it. I don’t need a relationship to keep my libido satisfied,” he smirked until he noticed the confused look Jack was giving him. “My point is that, while I don’t know why you're asking, you shouldn’t worry about relationships. You shouldn’t be in one anyway, you're like three. Now scram, before I say anything else I might regret.”

Jack took his advice and left. While he hadn’t gotten as much information like he had hoped, the conversation wasn’t pointless. He still held onto hope from the part when Dean talked about possibly having feelings for someone that would “never work out.” It could mean practically anyone, but Castiel was still a potential candidate.

However, Jack felt a little discouraged by how firmly Dean stated that he had no romantic feelings for anyone he currently knew. Which meant the first part could be talking about someone that he had once loved that had tragically died before Dean could confess anything. Jack felt really confused and not at all as reassured as he did with his conversation with Castiel. 

He was walking through the Bunker hallways as he thought about this when he ran into Sam, quite literally. 

“Woah, slow down bud,” Sam held out his hand to stop Jack from bumping into him head first. “Is everything alright? You look like you're in deep thought about something.”

Jack opened his mouth already preparing to brush Sam off and tell him that it was nothing, but he paused. Sam was Dean’s brother and he knew him better than anyone in the whole world, even more than Castiel. He might actually be able to help him out, at least indirectly.“Can I ask you something? It’s going to sound really weird, but you have to promise not to question it.”

“Uh, sure…” Sam told him, looking unsure. 

“If Dean was in love with somebody would he be honest about it?”

Sam blinked. “Okay… that was definitely not what I expected you to ask.”

“Just answer it,” Jack pushed, “And remember I can’t explain why.” 

Sam looked thought for a moment. “I guess Dean wouldn’t be straightforward about it. He doesn’t exactly like talking about his feelings. If he finds someone attractive he’s usually pretty open about it, but he’ll keep his mouth shut if he really feels strongly about them.”

“Would you be able to tell? Even if he was lying?” Jack thought back to the text Sam sent Claire. That’s what started all of this anyway. 

“Oh yeah. Dean thinks he keeps his feelings locked away, but he’s usually pretty obvious. At least to me he is,” Sam answered with a fond look in his eye. 

Jack felt relieved. That meant that Dean was definitely lying to him when he said he wasn’t interested in anyone and he was feeling pretty confident that the person was Castiel. After all, Sam told Claire that it was and the younger Winchester would know Dean’s feelings better than anyone. “Thank you Sam. You have been very helpful,” Jack gave him a polite smile before spinning on his heels intent on going back to his room. 

“Hold up Jack,” he was stopped by Sam grabbing his shoulder. “Look, I know you don’t want to tell me what’s going on and I’ll respect that. But you gotta know that Dean isn’t looking for a relationship right now. I mean yes he’s in a good place and I want more than anything to see him happy one day, but you can’t force this kind of thing. Dean is happy with the way things are and he’s not looking to change that. If one day he changes his mind, then that’s his decision. I know I might be way off here, but if I’m even a little bit right, then I’m telling you to let this go.”

Jack slowly nodded in return and saw relief wash over Sam’s face. The hunter gave his shoulder a squeeze and released him. Jack went back to his room feeling less excited about his talk with Sam. He replayed Sam’s final remarks in his head over and over. Sam’s assumption wasn’t entirely off, but Jack wasn’t ready to let this go. In fact he was just getting started. He dissected Sam’s words and came to his own conclusion. Dean’s issue was that he was content with the way things are and he didn’t want this to change. Jack interpreted that as he didn’t want to bring in a new person and ruin their established family dynamic. 

Dean’s exact words were that all he needed was himself, Sam, and Cas. But, with his and Claire’s plan, nothing would change. It wasn’t like he was trying to set Dean up with someone new that would disrupt everything. No, with their plan, their family would remain exactly the same. Yes, Dean and Cas’ new relationship would cause a slight shift in the dynamic, but it wasn’t a bad change. Jack could only imagine that it would make everything better. 

So, he decided to not take Sam’s words to heart feeling justified that he was doing the right thing. He decided to call Claire and tell her about the new information he just found out. At first, she was pissed that he did it without consulting her first, just like he expected. She told him that his plan was stupid, unorganized, and it could have ruined their whole opperation. She cooled down once he told her how successful he was (purposely leaving out his warning from Sam). She even applauded his ability to lie, “you’re becoming a true juvenile delinquent.” She also laughed at his straightforward questions, “I can’t believe they actually fell for it. I knew your innocence would come in handy one day.” 

She ended the conversation by informing him that she thought of their next plan, but she wanted Alex and Patience to be there when she explained it. Jack ended the conversation feeling actually excited about their next scheme. That night Jack fantasized about having two married parents like a normal kid. He imagined being a child in grade school asked to talk about his family to the class and him explaining to everyone that he lived with his two Dads and Uncle Sam. He knew he would never go to school, but the idea that part of that fantasy may become reality soon was enough to make him smile.


	7. Chapter 7

**Notes for the Chapter:**

> Sorry that this story took a long hiatus. Finals and a migraine kept me from updating, but now that I'm on summer break we should be back on track. To make up for it I give you a long chapter!

Jack hated Claire’s plan. 

“You said that you didn’t want a plan that involves lying and this doesn’t involve lying at all,” Claire pointed out.

“Yeah, but this could potentially be dangerous! I’d much rather lie than put people at risk!”

“Oh please,” Claire scoffed. “They can take care of themselves! Dean is a big scary hunter and Cas is an angel. There is no way they’ll get hurt.”

“It’s not them I’m worried about. If you piss them off they could seriously injure this guy. He doesn’t even know what he’s getting into.” 

“There’s no reason that this will get physical. Besides, Dean and Cas know better than to murder an innocent human in a public place.”

Jack and Claire had been going back and forth on this for the past hour. It was a big change from the excitement he felt when he started this conversation. That all disappeared when Claire told him her genius plan. 

She said she wanted to use the “make Dean jealous” strategy again since she liked the reaction they got last time which Jack didn’t understand. All they seemed to do last time was make Dean upset and put Jack into an awkward situation.

Her idea was to hire a stranger to flirt with Castiel at a bar and hopefully make Dean jealous. He tried asking where exactly they would get this “stranger” from and Claire brushed off his question by promising that she would take care of it. All Jack had to do was let her know the next time they all went to a bar with as much notice in advance as he could. Jack pointed out that the Winchesters never plan when they are going to a bar they usually just go, then a very frustrated Claire told him to try his best. 

Although Jack was thankful that his part in the plan was very small and it didn’t involve acting, he still had concerns. Who was this guy and where was Claire getting him from? Was he a hunter? Could they trust him? Jack couldn’t help but feel a surge of protectiveness for his father figure and the idea of purposely letting a strange guy come on to him rubbed him the wrong way. 

He voiced this concern to Claire who sighed, “I care about Castiel too. I would never pick someone who's an asshole, although he might have to act that way to catch Dean’s attention.” 

“How do we even know that Dean will react the way we want him to?” he asked. He had seen many women flirt with Dean and Castiel never reacted once, how do they know that Dean will be any different.

“Because Dean is fiercely protective when it comes to the people he cares about. Add that on top of a secret crush, insecurity over his sexuality, and his fragile masculinity and there is no way he won’t react.” Jack only understood half of what Claire said, but from what he got, he had to admit that her points were valid. “But if he doesn’t react, then we have to accept that it’s mission failed because you can’t intervene. If you intervene then this whole scheme could be easily traced back to us. Cas can take care of himself, so there’s no reason for you to be involved.” 

Jack thought about it for a minute. “What if Dean does react and things go bad?” 

“I already told you, Dean will be fine.” 

“It’s not Dean I’m worried about,” he mumbled. Jack knew firsthand just how scary the hunter could be when he was angry and the hunter was not afraid of causing a scene. 

“Jack it’s not that big of a deal. Everything will be fine, I promise.” 

Jack sighed. Claire had a point, there was nothing bad that could happen from this. Considering they were people that dealt with life or death situations in a daily, this should seem relatively mild in comparison. Safe or not, something about this plan still made Jack feel bad. “Fine, but I still don’t like it,” he relented, brushing off his worry as guilt for going behind their backs. 

“If it helps, I’ll let you get final say on the guy I pick,” Claire suggested kindly and Jack agreed. 

She called him back only two days later, after sending him a picture of a man in his later thirties. “His name is Sean, he’s a hunter, and he’s bisexual,” Claire listed off. “He’s worked with Jody on a few cases in the past and I’ve already met him more than once. He seems nice enough, as far as hunters go. He was in theater in high school, so his acting skills should be decent. He’s heard of the Winchesters before, but he has never met them. Which is good because it means they won’t recognize him and he’s just scared of them enough to not want to get on their bad side.” 

Jack thought it over. To be honest he was not sure what he was looking for. Everything Claire said made him seem trustworthy enough, but there was no way of knowing for sure without meeting him. The idea of arranging a meeting seemed like a lot more effort than it was worth, so he decided to trust Claire’s judgement. 

“Also, I already asked him and he said yes,” Claire added when Jack took too long to respond.

“How did you get him to agree?” Jack asked, genuinely curious. In his experience, hunters usually weren’t so generous unless they got something out of it. 

“It wasn’t that hard,” Claire shrugged. “Most hunters are broke, so I offered to pay him. They’ll do practically anything for a quick buck. Besides, Castiel is good looking so it’s not like this will be torture for him.” 

Jack didn’t know what to make of that last part, but he did agree that hunters are always in need of money. At least, Sam and Dean always seemed like they were. He gave Claire his consent to her choice and ended the call. 

The following weeks Jack stayed on alert for his part of the plan, which proved to be harder than he anticipated. The next few hunts Sam and Dean went on they left Jack and Castiel behind. During that time, the angel took Jack on a road trip of their own to restock the Bunker’s supply of ingredients used commonly in spells and summoning rituals. Once both pairs returned, it took another week for them to rest up and find a new case. 

Finally the four men were on the road following a lead on a vampires nest in Smithville, Missouri. Jack was staring out the window at the seemingly endless row of green trees when Dean spoke up. “Sweet, there’s a bar across the street from our motel. We’re definitely checking that out before we leave.” That caught Jack’s attention as he suddenly took note that they were just outside of the city limit. 

“The Green Tavern?” Sam read the sign outloud. “Isn’t that a popular hunters joint?” 

“You’re right!” Dean exclaimed like he just remembered. “We’ve been here a couple of times years ago.” Jack pulled out his phone and sent out a text to Claire, since this was probably the most in advanced notice he could possibly give. She responded thanking him and telling him that she'll have her guy on standby. 

The hunt took a total of three days, and Jack’s mind was way too preoccupied to put too much thought into his and Claire’s scheme. He only gave her short update responses the few times he noticed her messages. On the evening of the third day while they were preparing to raid the nest, Jack sent out a short text to Claire telling her that it will probably be tonight as long as everything goes well. The Winchesters were big believers in buying victory beer, or at least Dean was. 

By the time 11:00 rang and they were headed to the bar, Jack had nearly forgotten about the plan entirely, his mind too busy replaying the night's events.

The vampire nest was located in an old abandoned warehouse where ten vampires were squatting inside. Sam and Dean came through the front entrance and easily killed off two the moment they entered drawing the others attention towards them. This gave Castiel and Jack the opportunity to sneak in through the back entrance without any of them noticing. Castiel swiftly beheaded two vamps from behind and Jack one, before they were seen. That’s when all hell broke loose now that all the blood suckers were on high alert. There was a vampire for each of them and they were not going down without putting up a good fight. The monsters were strong, but they were no match against their team. 

Unfortunately, they had miscounted the number of vamps as one had remained hidden, watching the fight. He got the jump on Jack the moment after he had beheaded the one he was fighting. He roughly grabbed him from behind, his tight one-armed grip locked his elbows to his side. With his other hand the vampire pressed a knife against Jack’s throat. The nephilim internally cursed when he noticed it was an angel blade and wondered where he had gotten it. Sam or Dean must have dropped it during the fight. 

“Drop your weapons or the boy gets it,” the vamp sneered. Sam, Dean, and Castiel, having already killed the other vampires, turned and looked at Jack with surprise. 

“Going after the youngest, you know that’s the cowards way out? Why don’t you come over here and fight like a real man? At least, then you’ll die with dignity,” Dean said cooly, not showing any sign of fear.

“I said put your weapons on the ground! Now!” he put pressure on the knife, directly over his larynx. “Don’t think that I won’t do it!” Jack winced when he felt the blade drew blood. He knew he was in no danger since the blade wasn’t strong enough to actually kill him, but it still stung. 

“Please. He’s just a kid,” Sam voice wavered, with what Jack recognized as fake fear. Still, the trio complied and slowly placed their weapons on the ground. 

“Yeah, well next time don’t bring junior on a hunt,” the monster scoffed. Clearly, he believed he had the upper hand. “Now, put your hands behind your head!” 

“I wouldn’t be so sure…” Castiel mumbled as he followed the two hunters and put his hands behind his head. Jack knew their plan the minute he sensed that their easy obedience was merely an act. See, the thing about cowards was that the minute they feel comfortable is when they become cocky. And when they’re cocky, they make mistakes. 

Jack weakly struggled against his hold to keep up appearances, while he waited for his cue. “Yeah whatever, start heading towards the door!” he barked, not releasing his hold on Jack. 

They slowly inched backwards in the direction of the door. “What about the kid?” Sam asked after taking two small steps. 

“Nah, I think I’ll keep him,” Jack felt the man’s warm breath on the back of his neck, sending a chill down his spine. “I think he’ll be a great snack. It’ll be fun to drink him nice and slow.” The vamp buried his face in the crook of Jack’s neck and took a deep inhale. Jack cringed as he felt a tongue lick his bare skin. Thankfully, his grip on Jack was starting to loosen up after he pulled their bodies closer together. The vampire clearly thought he had the upper hand.

Jack saw both of Sam and Dean’s faces darken. “Big mistake,” Sam spat. 

“I’m not afraid of you,” the vamp scoffed. 

“It’s not us you should be afraid of,” Sam returned. Their backs were nearly to the warehouse door. 

“See, you might think he’s stuck in here with you, but really you’re stuck in here with him,” Dean said darkly and Jack knew that was his cue. Without hesitation Jack elbowed the vamp in the stomach and broke free of his hold. Before the monster could even react, Jack had the palm of his hand on his forehead. The nephilim focused all of his energy and rage into the bright light emitting from his palm. Seconds later, the bright light was gone and the two hunters and the angel were at his side staring down at the corpse laying at his feet. It was unrecognizable now that the head had been burnt to a crisp. 

Dean reached him first, but he went straight past him sending a hard kick to the dead body on the ground. “Creepy… ass… son of a… bitch…” Dean growled in between kicks. Until Sam roughly grabbed his brother by the arm making him stop. 

“I’m pretty sure he’s dead Dean,” 

“Are you okay Jack,” Castiel asked, looking him over. 

“I think I’m okay,” he answered honestly. The small cut on his neck had already healed over and otherwise he hadn’t been physically harmed. “Did I do alright? I lost control for a second.”

Sam put a comforting hand on his shoulder, “You did good Jack. That man deserved it and he probably would’ve hurt more people if he’d gotten away.” 

“Yeah and least you killed him quick,” Dean chuckled. “If you would’ve left him to us we’d have killed him real slow —“ Dean stopped when Sam punched his arm and gave him a look. 

Jack didn’t remember Claire’s plan until the Impala pulled into a parking spot and the green neon lights were shining in his face. He sent her a quick text telling her where they were, then tried to listen to the conversation Sam and Dean were having in low voices. 

“Are you sure about this?” Sam asked his brother, voice laced with concern. 

“Why not?” Dean shrugged. “I promised the kid a beer and he earned it.”

“Yeah, but this a popular hunters bar and hunters are known for being kinda… shady,” Sam said tensely. “I mean it was fine when we went, but are you sure about bringing Cas and Jack here?”

“They’ll be fine, they’re with us. All we have to drop the name Winchester and we’ll have the whole room eating out the palm of our hands,” Dean said with a smirk. Then he hoped out of the car before Sam could argue any further. Jack let out a breath of relief. Claire told him the guy was already there and he wasn’t sure what he’d do if they suddenly decided to go somewhere else. 

Jack followed behind as they walked into the bar and took a seat at a booth in the back corner. He automatically took a seat next to Castiel and checked his phone when he felt it vibrate. It was Claire telling him to try and get Cas by himself. He felt his anxiety levels raising as he wondered how he would accomplish that. Part of him wanted to back out of the plan right then, the leftover stress from the hunt and now this was starting to get to him. He knew that if he told Dean he wanted to go back to the motel they would take him in a second, but a part of him preferred doing this now instead of holding it off for another week. 

He was pulled from his thoughts when he heard Dean loudly say his name. He looked up to see all three of them staring at him with worried looks. 

“Are you okay?” the angel asked, putting a comforting hand on his arm. 

“I’m fine,” he insisted, not wanting to screw this up. “What did you say?” he turned to Dean. 

“I said I was going to grab a pitcher of beer. Did you want anything else?” the hunter answered, still looking concerned. 

“Can I have French fries?” he said, realizing that he actually did feel hungry. Maybe he could eat away his nerves.

“Coming right up,” Dean gave him one last look before walking away. Jack realized this was the perfect time to enact Claire’s plan since Dean had already left. Now, to get rid of himself and Sam.

Noticing the way Castiel began to open his mouth - probably to ask about Jack’s well being again - he decided to interrupt. “I have to pee,” he said suddenly.

Sam raised his eyebrows,“Ok?” Then his face relaxed, “Actually, I think I’ll go with you.” Jack nodded, happy that at least this part of the plan was going right.

He let Sam lead the way to the men’s bathroom as he slowly trailed behind. He had no idea how much time he needed to waste, so he would try to drag this out as long as he could. Also, he prefered not to be there when it happened, since he knew it might make him feel guilty.

Unfortunately there was no line for the bathroom like he hoped, which meant he’d have to try and take as long as possible without drawing suspicion from Sam. He slowly washed his hands for at least double the 20 seconds suggested on the sign above the sink, making sure to clean up the dried blood under his fingernails from the vampire he killed earlier that night. He left his hands under the air dryer until they felt hot, ignoring the impatient looks he got from Sam and the 30 year old man waiting behind him. But even with all of his lingering, the trip couldn’t have lasted over five minutes. 

Accepting his defeat he headed for the door, but Sam stopped him, “Jack, can I talk to you for a minute?” He nodded, grateful for any excuse to waste more time. “Are you okay? You seem a little off.”

“I’m okay,” he said quickly, already expecting Sam to ask this. “I’m just tired.”

“You know that you can always talk to me?” Sam said with a sincere expression. “Back at the warehouse, it must’ve been pretty scary when that vampire grabbed you. Years of hunting, and it still throws me for a loop when it happens.”

“He made me feel uncomfortable and I knew that he wanted to hurt me, but I wasn’t scared,” Jack answered honestly. “I knew that I could overpower him and that I was strong enough to kill him on my own. He wanted to take me, but even if I didn’t have powers, I know that you, Dean, and Cas would never let that happen.”

“No we wouldn’t,” Sam gave him a little smile. “Look, I know Dean seemed pretty excited about coming here tonight, but we don’t have to stay if you don’t want to. If you’re tired or feeling strung out after the hunt, Dean will understand if you don’t want to stay. Just say the word and we’ll take you back to the motel.”

“Thank you Sam. I appreciate your concern, but I think I would like to stay,” he gave Sam an honest smile. He really did appreciate his worry and he might have even taken him up on the offer if it weren’t for Claire’s plan. Bars were noisy and filled with inebriated people, going back to the motel for a quiet night in with just the four of them was preferable. “It helps to take my mind off things,” he lied, wishing he was anywhere else.

Sam and Jack walked out of the men’s bathroom, both identically stopping in their tracks when they saw the unfamiliar man standing at their table. “Who is that?” Sam asked, confused.

“I don’t know,” Jack lied. He immediately recognized the man from the photo Claire had sent him. The man looked a little more rugged than he did in the picture, but there was no mistaking him. He was staring at Castiel with a cheeky grin while the angel stared at him with a furrowed brow, sitting in the same spot they left him. 

Sam cautiously walked towards the table and Jack followed behind him. “Hey Cas, who’s your friend?” Sam asked awkwardly, not taking a seat. Jack decided to follow his lead, taking advantage of Sam’s tall stature to hide behind. 

Cas looked annoyed, “He’s not my fr-”

“Names Sean,” the guy interrupted, Jack took notice of the lack of a fake name. “I was just talking to your handsome friend, and was wondering if he wanted to get outta here?” 

“And I said no,” Castiel said firmly, finishing for him. 

“Come on, don’t be like that. You can’t actually want to stay here with these guys.” Sean gestured towards him and Sam. 

“Actually, I would very much prefer to stay with my friends than go anywhere with you,” Cas said with a very serious face.

“Come on sweetheart,” the man pressed. “I got a motel room across the street, the rooms next mine are vacant which means we can make all the noise we want,” he said with a dirty smirk.

Castiel rolled his eyes irritably, but before he could comment a voice from behind Sean spoke up. “I’m pretty sure he told you no,” Dean said calmly, “so scram.” He moved past the guy, placing the pitcher of beer and basket of fries on the table. 

“What are you? His boyfriend?” Sean scoffed looking Dean up and down.

“Nope. I’m just his friend who doesn’t like douchebags,” Dean’s demeanor was relaxed, but he had a warning look behind his eyes. 

“Then I guess it’s not your business if I want to talk to your hot friend,” he fired back. Sam, Cas, and Jack all seemed to be frozen, anxiously watching to see what Dean would do. 

“Don’t do this. We’re just trying to have a good time.” Dean gave him one last attempt at a peaceful resolution. “Go harass someone else, but not us and not him. I mean, his kid is watching. He doesn’t want to hear you say gross shit about his dad.” 

“Well you should’ve thought of that before bringing him to a skeevy bar. This isn’t Applebee’s.” Jack had to internally applaud the man for his persistence and commitment to this character. He seemed fully intent on not backing down without a fight. “Besides he seems old enough to know that the world isn’t all sunshine and rainbows.”

“Wow thanks for the lesson now leave us alone. Don’t make me ask again.” 

“Or what? Are you going to stop me?” the man crossed his arms and remained firmly rooted in front of their table. 

“Look, I’m guessing you’re a hunter right? You have that vibe, with your flannel and ‘I’m not scared of anything’ act,” Dean chuckled, giving him a once over. “And that’s all it is. An act. Cause if you knew who we really were, then you would be too scared to even walk into this bar.” 

“Who are you?” The man tried to keep his confidence from earlier, but Jack didn’t miss the brief flash of hesitancy on his face. He didn’t blame him for his reluctance, because Sean knew exactly who was standing in front of him. 

“Dean,” Sam spoke up with a warning look towards his brother.

“No, I got this Sam,” Dean held up his hand while his eyes never broke contact from Sean. “We’re the freakin’ Winchesters. The same guys who started and stopped the apocalypse. That have defeated the devil and death multiple times. Who have looked into the eyes of God himself and told him to shove it.”

“Laying it on a little thick Dean,” Sam muttered under his breath low enough that only Jack heard it.

“T-those are just legends,” Sean said weakly. 

“You really want to take that bet?” Dean seemed to be towering over him. “Now, fuck off.” 

Sean put his hands up in surrender. “Okay, I’m backing off.” Then he finally walked away from their table. Jack let out a breath of air that he hadn’t realized he’d been holding. He followed Sam and Dean’s lead and sat back down in their original spots. 

“What the hell was that Dean?” Sam said as soon as they sat down. “You were acting kinda over aggressive.”

“He was being a dick,” Dean shrugged, pouring himself a glass of beer.

“Yeah, but was it really necessary to pull the ‘we started the apocalypse' card,” Sam reprimanded causing his brother to roll his eyes. 

“He was harassing Cas and I wanted his ugly mug outta my face as fast as possible. Intimidation was the only idea I had that wasn’t ripping his throat out.” Dean chugged his glass before moving to pour himself another one earning him a grimace from Sam. 

“Dude dial back on the possessiveness. He was just flirting, that’s what people do at bars. It’s not like he was actually trying to hurt him.” 

“I’m not possessive and that was not flirting. We all wanted him gone and it’s not like you were going to say anything to him. When I got here all three of you looked like deer caught in headlights.” 

“I didn’t need your help. I can take care of myself.” Castiel finally spoke up and he did not sound happy. 

“Yeah I’m sure you can. You really looked like you had a handle on things before I came,” Dean shot back sarcastically. 

“Need I remind you that I am a celestial being with power a hundred times stronger than a mere human like you,” the angel growled. 

Dean scoffed. “Yeah because smiting a dude in a room full of hunters is considered taking good care of yourself.” 

“I could have used words and argued with him the same way you did,” Cas said indignantly.

Dean tsked, “Sorry buddy, but I’ve known you for ten years and I know that you have a history of letting people walk all over you.” Castiel glared daggers towards the oldest Winchester.

Jack went to check his phone, knowing that this argument could last for hours. He saw a text from Claire telling him to call her when it was done. Wanting nothing more than to be anywhere else he realized that calling Claire was the perfect excuse for him to leave. 

He mumbled that he had to go to the bathroom, before standing up to go to a quieter area of the bar. Thankfully, Sam, Dean, and Cas were too busy arguing to question him going again in a matter of ten minutes. Jack walked with his head down looking at his phone as he scrolled through his contacts searching for Claire’s name. Unfortunately that meant he wasn’t paying attention before someone shoved him against the wall. His eyes widened when he saw that his assaulter had been Sean. 

“You made me look like a fool back there,” he growled, pressing Jack further into the wall. “Now I’m on Dean Winchester’s black list for the rest of my life.” 

“It’s not like he’ll come after you. He just doesn’t like you very much,” Jack said weakly. 

“I did whatever dumb shit you wanted me to. Now it’s time to pay up.” Jack’s eyes widened, Claire never mentioned that he was supposed to pay him. He didn’t have any money and even if he did he didn’t know the amount she promised him. 

“I-I can’t. Claire’s supposed to be the one to pay you,” he told him. 

Sean scoffed. “Why? So that I can waste my time hunting her down and never get my money? No, I’d rather get it from you now.” 

“I-I don’t have it,” Jack admitted. 

“Don’t lie to me kid,” he roughly pushed Jack against the wall one more time causing his head to bump into it. Jack winced at the sharp pain now spreading on the back of his head. 

“I’m not lying. I don’t have any money.” Jack was starting to get annoyed. He needed to reign in his emotions or else he might lose control. If he became too upset he could unintentionally set off his powers. 

“Fine. Then I’ll walk back over there, tell the Winchesters that you hired me, then they can pay me the money themselves.” The idea that Sean would sell him out and ruin their plan made Jack’s stomach feel uneasy, but he refused to show his nerves. 

“As if you’d ever be brave enough to ask Dean Winchester for money,” Jack spat. 

“You want to bet on it?” Sean tried being intimidating by shaking him a little. 

“Fine. Do it,” Jack said calmly with a hint of a smirk. “I’ll just lie and deny everything you say. Let’s see who they believe. Some random scumbag they met in a bar who is asking them for money. Or the young boy they raised and consider to be like a son. Sure, I’m willing to take that bet.” 

The nephilim felt quite satisfied with his comeback, but it only seemed to make the hunter more mad, “You little punk. I’m getting my reward even if I have to cut it out of you.” In a flash Sean pulled out a knife and pressed it against his cheek. Jack scrambled his brain to come up with a plan to get away from him without causing a scene. Using his powers was out of the question considering Dean’s comment about how it was a bad idea to smite in a room full of hunters. 

Before Jack could come up with a plan, he felt Sean being pulled off of him. He relaxed a little when he saw it was Dean, with Sam and Castiel not too far behind him. Dean looked beyond pissed and didn’t hesitate to punch Sean square in the face. Sean weakly swung his fist in a lame attempt at retaliation that the Winchester swiftly dodged. Dean then threw another punch that hit its mark across Sean’s left cheek knocking him to the floor. 

“Didn’t I tell you? Don’t fuck with us.” Dean said glaring down at the man sprawled on the floor. 

“No fighting!” The bartender barked at them from across the bar. 

“Yeah yeah. We’re leaving anyway.” Dean yelled back. 

“I told you I’d win that bet,” Jack couldn’t stop himself from saying with a cheerful smile. He was just glad that the guy got what he deserved. 

“I’ll fucking kill you,” he growled as he shakily stood up and lunged towards Jack. Before he could react, Castiel swiftly stepped in front of him and put two fingers to Sean’s forehead. The hunter's eyes rolled to the back of his head as he immediately collapsed to the ground. 

“Come on,” Sam grabbed his arm and gently pulled him towards the door. 

“I’m so tired of dealing with creeps today,” Dean muttered grumpily. 

The drive back to the motel was filled with tense silence, none of them daring to break it. It wasn’t until the car pulled to a stop in front of their motel room that Dean decided to speak up. 

“Alright, go ahead and say it. I know you’re dying to,” Dean sighed. 

“Say what?” Sam sounded surprised. 

“You know what I mean. Give me a lecture about how I overreacted and shouldn’t have punched that guy in the face. Your usual Sam crap about how violence is never the answer.” 

“Actually I wasn’t going to say anything,” Sam shrugged looking down at his lap. 

Dean raised his eyebrows. “Really? You don’t disagree with what I did?” 

“Honestly? I probably would’ve done the same thing if I had gotten to him first,” Sam said casually. Dean raised his eyebrows, so he clarified. “Look, you can be pretty overprotective sometimes, but that doesn’t mean you’re never valid. He physically attacked Jack obviously you had to step in.”

“Okay so Cas can take care of himself, but the kid is where you draw the line? Alright Sammy I can respect that,” Dean said he agreed with his brother, but his tone suggested otherwise. “What about you sunshine? Are you going to tell me that Jack can take care of himself?” He glanced at Cas through the rear view mirror.

“You may have been the one to hit him, but I was the one to knock him out. So no, I can’t say I disagreed with your actions,” Castiel sighed. “As for Jack, I think he proved that he is more than capable of taking care of himself back at the warehouse. However, as we already established, burning a person to death in a room full of hunters is less than ideal. I think your intervention was appropriate.” And even Jack had to agree with that.

While he was grateful that Castiel gave him recognition for saving himself from the vampire, he was also glad that Dean stepped in when he did. He couldn’t think of a scenario where he escaped without using his powers and Dean “saving” him made the most reasonable sense to an outsider like Sean. He knew that in Sean’s eyes he probably looked like a helpless young boy who was new to the hunting life, if only Sean knew just how far he was from the truth. 

“Well it’s good to know everyone agrees with me for once,” Dean groaned. “What about you Jack? Are you okay?” Dean glanced at him through the rearview mirror. 

“Yes, I’m fine,” Jack said honestly. Sean didn’t scare him for a second, he knew the man was too big of a coward to ever actually hurt him. Even if he did succeed it would’ve been the last thing he ever did. Jack knew he could stop him with a blink of an eye if necessary and either way the Winchesters and Castiel could easily kick his ass. 

“What did he want with you anyway? He seemed pretty pissed,” Dean asked him. 

“I think he was just mad that you embarrassed him. I guess he saw me and thought he could get payback,” Jack lied easily. He’d already been prepared to be asked that question.

“Before we left you said something about winning a bet, what was that about?” Sam asked him. Jack internally cursed himself for not being more careful. He was less prepared to answer this, but he still came up with a believable story. 

“I told him that if he tried messing with me Dean would kick his ass,” Jack said with a grin. 

“Fuck yeah,” Dean reached his hand to the back seat for a high five. Jack slapped his hand with a laugh. “Alright, I’m sick of this place. I say let’s leave now before we run into anymore assholes.”

“Are you sure?” Sam asked. “It’s pretty late. Are you feeling up to driving four hours right now?”

“Are you kidding? I’m running on beer and adrenaline. I feel fantastic.” Dean gave his brother a wink. 

Jack helped Sam and Cas load all of their stuff back into the trunk of the Impala while Dean left them to check out. Once he came back they hopped in the car to start their journey home. 

“Sam do you mind switching with Cas?” Dean asked while he warmed up the car. “I need a passenger that will help keep me awake and you look like you’re about to knock out.” 

Sam agreed with a shrug before getting out to move to the back seat. 

“I can stay awake with you Dean,” Jack offered. “I’m half angel which means I only need half the sleep.” 

“No way kiddo. You’re hopping on the snooze train with Sam,” Dean said adamantly. “Last time you tried pulling an all nighter you ate a ton of sugar to help you stay up and you were bouncing off the walls till noon.” 

Jack pouted then slumped back into his seat. He pulled out his phone and sent a text to Claire telling her that he won’t be able to call her until the morning. Then he obediently curled up against the car door and closed his eyes. He didn’t have a lot of room to put his feet on the seat with Sam sprawled out next to him. 

He didn’t feel that sleepy, so he decided to think about what he would tell Claire. Things didn’t go exactly to plan and he should probably warn her that if she ever ran into Sean again he might be angry. He also wasn’t sure if they’d gotten the reaction from Dean that they wanted. 

Dean came to Cas’ defense as they had hoped, but he didn’t really seem jealous. Dean was overprotective when it came to people he cared about, so who’s to say it was any different from him saving Jack? In his opinion, all they managed to do was cause a fight between Dean and Cas. Now the pair seemed further from romance than ever. 

“Hey Cas,” Jack perked up when he heard Dean speak from the front seat. “I’m sorry for implying that you can’t take care of yourself and I’m sorry for saying that you let people walk all over you. That was a dick move.” 

“Yes, it was,” he heard Castiel say stiffly. 

“Look,” Dean sighed. “I’ll apologize for being a dick to you, but I won’t apologize for protecting my family and that includes you and the kid. I don’t care how annoying you all think I am.” 

“I don’t think it’s annoying,” Castiel said so softly that Jack nearly missed it. 

“Really?” Dean sounded surprised. 

“I think it’s… sweet.” There was a long silence that followed Castiel’s answer. Jack had to fight the urge to open his eyes and see the look on their faces. However, he knew that he couldn’t let them know that he was awake or else the moment would be ruined. 

“Um... thanks I guess,” Dean mumbled awkwardly. 

“Although, I still think you overreacted,” Castiel said, truly breaking the moment. 

“If he didn’t want me to fight him then he shouldn’t have walked up to our table in the first place,” Dean grunted. 

“Oh please, as if he could have known that you would react that way,” Castiel sounded as if he thought Dean was being ridiculous. 

“You were at a table with your friends, it was obvious that you weren’t looking for company.” 

“Actually, when he first walked over I was sitting by myself,” Castiel pointed out. 

“Fine, but that doesn’t give him a right to make a pass at you,” Dean sounded like he was getting increasingly annoyed by this conversation.

“Why not? I don’t see how it's any different than what you do in bars,” Castiel skillfully hid the insult under a layer of what sounded like innocence and Jack couldn’t help his admiration of his father figure’s wit.

“It’s different because the girls I hit on are into it,” Dean defended himself lamely.

“What if I was into it? Would it be so bad? It’s not like you gave me a chance to speak for myself,” Castiel challenged. The angel’s question made even Jack anxious for Dean’s reply. 

“Seriously? Are you even gay Cas?” Dean sounded in disbelief.

“Gender is a human social construct Dean, it’s absolutely meaningless to something like me. You still didn’t answer my question,” the angel pressed. 

“Whatever dude, go ahead and fuck whoever you want! I couldn’t care less!” Dean long abandoned trying to talk quietly and at this point was just trying not to yell.

“Why does this bother you so much?” Cas sounded genuinely curious and on the brink of concern. 

“Because -” Dean started hesitantly, but was soon interrupted. 

“Dude shut up! Some of us are trying to sleep!” Sam whined from his sleeping position. 

“Oh excuse me for interrupting your beauty sleep Samantha,” Dean mocked his brother. 

It was at this point Jack decided to “wake up.” It didn’t make sense for him to keep pretending anyway. If Dean and Cas were being loud enough to wake up Sam logically the same noise would wake Jack up too. He wasn’t exactly a light sleeper. “What’s going on?” Jack asked eagerly, sitting up straight. 

“Great Sam, you woke up the kid,” Dean said exasperated. 

“It wasn’t me. It was the old married couple up front,” the younger Winchester murmured from his sleeping position with his eyes still shut. 

“What were you arguing about?” Jack asked innocently, despite having heard their whole conversation. 

“We weren’t arguing Jack, we were just talking,” Castiel lied. 

“Yeah, now go back to sleep,” Dean ordered. 

“I already slept long enough,” the nephilim protested even though he didn’t sleep at all. 

“It’s only been like 45 minutes,” Dean pointed out.

“But I’m half angel. That means 45 minutes is equal to two hours,” Jack said as if it was a fact. 

“All that tells me is that Sam needs to teach you math because that’s not even close to being right,” Dean argued. “Now let’s say that your half human theory is right. That would mean you only need to sleep half the amount of a normal human. Except, you’re only three years old and three year old humans need like twelve hours of sleep. Which means you still need six hours. So, in five hours you can wake up.” 

Jack pouted. “Fine,” he relented knowing this was a losing battle from the beginning. This time he planned on actually falling asleep since he felt a lot more content after overhearing Dean and Cas’ conversation. He was finally starting to understand what Claire meant when she said that arguing could lead them to talking out their feelings. They had seemed like they were making great progress until Sam interrupted. 

With that thought Jack curled up against the car door letting the low sound of Bob Dylan on the radio and the familiar purr of the engine lull him to sleep. 

**Notes for the Chapter:**

> More Claire next chapter! Also an appearance by my Queen Rowena!


	8. Chapter 8

“Really nice guy you found Claire,” Jack said sarcastically the moment her face appeared on his laptop screen. After they returned from the hunt in Missouri, Jack made plans to video chat Claire that evening. He had closed his bedroom door before calling in case someone tried walking in, although he doubted that anyone would. The other Bunker residents usually kept to themselves during this time of day.

“Oh no, what happened?” Claire grimaced. Jack retold the entire story. Mainly focusing on the part where Sean cornered him, Dean punched him in the face, and they were kicked out of the bar. 

“You need to be careful when you go to pay him because he is really angry,” Jack warned her.

“As if he could ever track me down,” Claire said with a smirk. 

“You mean you’re not planning on paying him?” Jack’s eyes widened. 

“I promised him like $500 and I don’t have that kind money,” the blonde shrugged like it was no big deal.

“Then why would you —“ Jack paused when he realized, “Oh — you were never going to pay him anything.” 

“I mean I always thought he was an asshole, but now you gave me more reason to believe that,” Claire said casually. “Now I don’t feel bad for scamming him.” 

“Wait a minute,” he suddenly remembered something Claire said earlier, “You told me that he was a nice guy. That he was just going to pretend to be a dick.” He felt a little betrayed. She swore that Sean was a good person and Jack trusted her. Now she basically admitted that she lied to his face. That’s why he hated lies — someone always ends up hurt. 

“Okay fine I may have exaggerated my description a bit,” Claire confessed. “I wanted you to go along with my plan and the only way you’d do that is if you believed he was good. So fine, I lied about him taking drama in high school, but he’s a hunter, obviously he knows how to lie. Also, he may have only worked with Jody on two hunts, and he did seem kind of a dick, but most hunters are.” 

“They are?” Jack asked, surprised. He thought back on all of the hunters he knew. Sam, Dean, Claire, Jody, Mary, Bobby, Maggie… they were good people. “All the ones I’ve met seem alright.”

“Of course they were,” Claire scoffed. “The Winchesters may be big in the hunting community, but they only have a small circle of people they actually trust. I’m sure everyone you know is in that circle because they wouldn’t let you near anyone they knew was a dick. They can’t risk the wrong person finding out that you’re the son of satan.”

Jack had to admit that Claire made a fair point. When he thought about it, some of the apocalypse world hunters weren’t the nicest, but Sam always told him that they were just nervous because he was part angel. After all, they treated Castiel and Dean in a similar manner. He didn’t blame them since he saw how badly they were terrorized by Michael and his followers. Jack always figured that was just what living in an apocalypse world does to a person. He never considered that hunters from their world might act that way too.

“Fine, but I still think it would’ve gone a lot better if you picked someone that was nice,” Jack huffed. 

“Well you did say that Dean hates him now right? I’d feel more guilty if I manipulated Dean into hating a good person,” Claire pointed out. Jack could agree with that reasoning, but a small part of him wanted to continue to sulk. He was still slightly bitter about her deceit.

The blonde’s face softened, “Look I’m sorry that I lied and that Sean was a piece of shit, but at least everything worked out in the end. You’re fine, Dean and Cas are fine, Sean probably has a broken nose, but he’s alive.” 

“I guess you’re right,” Jack sighed.

“Okay now enough with the suspense. Did it work? Was Dean jealous?” Claire asked eagerly. 

“I didn’t think so at first but…” Jack then recounted the conversation he overheard between Dean and Cas on the car ride home. He also told her that he was starting to understand what she meant about jealousy leading to productive conversation. 

“I knew it!” Claire laughed in excitement. “They got so close! If only Sam didn’t interrupt, it would’ve worked!” 

“So what’s our next move?” Jack asked, curious. 

“I don’t know, but it has to be big,” Claire bite her lip in concentration. “Okay, so last time it would’ve worked if Sam hadn’t interrupted. So, we just need to get them to sit down and talk.” 

“That’s going to be impossible. They hate talking about their feelings,” Jack scrunched his nose. 

“I know, that’s why I need your help. I can’t come up with every idea by myself,” Claire told him, sounding mildly frustrated. 

“I don’t know what to do. I don’t know anything about romance,” he told her, feeling a little helpless. 

“You have powers. There’s got to be something you can do that will be useful.” 

“There isn’t much I can do,” Jack shrugged. “Besides killing monsters and this - “ he raised his hand towards his desk and levitated a pencil laying on top towards him. Once it hovered in front of him, he floated it around in front of the webcam for Claire to see before catching it in his hand. 

“That would be so much cooler if it wasn’t so useless to us,” she deadpanned. “There’s really nothing else you can do?” She asked, sounding desperate. 

“No, I can do more, it's just that my powers are… unreliable,” he sighed, trying to think of a good way to explain his predicament. “Sometimes they do what I want and sometimes they don’t. Most of the time it’s instinctual, it just happens. Either way, I don’t know what could be useful and I don’t want to risk Dean and Cas’ heads. Besides, anything I can do, I would need to be within close proximity and it would be easily traced back to me.” 

“Ugh,” Claire groaned. “There must be something we can do. I mean we have more knowledge than most people our age. You practically live in a supernatural library. That’s gotta count for something.” 

“Are you thinking about using… magic?” he asked, forming an idea of his own. 

“I don’t know, maybe?” She rolled her eyes, “Except neither of us know anything about witchcraft and even if we did it would be too dangerous for us to try.” 

“What if we got someone who did know witchcraft?” Jack suggested. 

“You mean a witch?” Claire’s eyes widened. “No way. We can’t trust a witch we’ll get screwed over.” 

“What if I knew a witch that we can trust,” Jack said with a grin. He was already formulating a plan in his mind. 

Claire chewed her lip, “I don’t know Jack,” she paused looking at him unsure, “you don’t exactly seem like the best judge of character.” 

The nephilim huffed, “You said it yourself, I don’t know anyone outside of Sam and Dean’s circle. Besides, last time you picked the person he threatened me with a knife. I think it’s my turn.” Jack gave her a smug look when she sighed in defeat. 

“Fine, but I’m not letting you meet with this witch alone,” she told him sharply. 

“You can come, but even if you didn’t I would be perfectly safe,” he reassured her. 

Claire chuckled, “Don’t act so cocky. You don’t even know if she’ll help us.”

“She’ll help us. I know she will,” Jack said with full confidence.

  
  
  


That’s how Claire found herself parked outside of the Bunker a week later. She was picking Jack up so that they could meet with the witch together. She looked down at the phone and sighed when she saw that it had been ten minutes since she texted the boy that she was there. When she talked to Jack earlier he seemed worried about lying to the Winchesters about where he was going. She was beginning to worry about if that’s what was taking him so long. 

She looked up as she heard the loud creak of the Bunker door opening fully expecting to see Jack walk out, instead she was greeted by the sight of Dean Winchester himself. When he looked in her direction she immediately ducked out of instinct. She had no idea what Jack had told him or why he came outside.

Claire knew she had been caught when she heard the crunch of gravel under boots headed in her direction. That didn’t stop her from wincing at the sound of a knock on her car window. Unsurprisingly when she looked up she was greeted by the sight of Dean wearing a shit eating grin on his face. With a sigh she rolled down the window. 

“You know if you’re trying to avoid someone, parking in front of where they live is a bad move. Especially when you’re the only car on the street,” he said the moment her window was down.

“Hi Dean,” Claire gritted out through a fake smile. 

“Hey kid,” Dean paused, looking at her like he was waiting for an explanation. When Claire refused to give one he continued, “Alright, so I guess we’re just going to pretend that you’re  _ not _ acting weird. Uh… Jack should be ready soon. He was watching Scooby Doo and lost track of time. Little twerp just had to know who was behind the faceless phantom.” 

“You were watching it with him, weren’t you?” Claire teased with a knowing smirk. 

“Shut up, it’s a good show,” Dean snapped and Claire laughed. “Anyway,” the elder hunter continued, “I thought I’d be polite and see how you’re doing.” 

“I’m fine,” Claire shrugged. 

Dean huffed, “Look Jack just told me that you guys were hanging out and I didn’t think anything of it until I caught you being suspicious. So, should I be worried?” 

“Just because he’s with me doesn’t mean we’re going to do anything bad. We’ll probably just go to a mall, eat junk food, normal stuff. I promise to return him with his nose clean,” she told him with what she hoped was a reassuring smile. 

“Well that’s too bad. I was kinda hoping you’d get him into a little bit of trouble. The kid needs to loosen up, I don’t want him to end up with a stick in his ass like Sam,” he said with a playful grin. 

“I never know what you want from me Winchester,” Claire said, surprised. 

“Honestly? As long as no one is dead or in jail,” he chuckled. “Just don’t tell Cas I said that,” he added, looking frightened as if the angel had heard him.

“I think I can manage that.” 

They both glanced when Jack finally appeared from the Bunker’s entrance. “Take care, kid,” Dean slapped the top of her car before heading back towards the Bunker. When he passed Jack he ruffled his hair earning him a scowl from the nephilim. 

Jack opened the passenger door and looked at her with a dorky grin. 

“Hello!” 

Claire gave him a smile in return as she watched him fumble his way into the car. 

“Did you have to be so honest to Dean?” she rounded on him the moment he was settled. 

“I thought I did good,” Jack said, a little offended. “I told him I was with you, but I didn’t tell him what we were doing.” 

Claire rolled her eyes as she started the engine, “I don’t even tell Jody where I go half the time, I just leave. As long as I come home at some point she doesn’t care.” 

“I guess we're just different,” Jack shrugged. “If I just left without saying anything Sam, Dean, and Cas would be worried. They might think something bad had happened and then they’d go look for me.”

“And we can’t have that,” Claire finished with a sigh. “In that case, I guess your lie was okay,” she was too stubborn to give him full satisfaction. “Any chance they might track your phone?” she asked certain that Castiel was the type of overprotective parent to have access to Jack’s location at all times. 

“I’m not sure,” Jack frowned before shaking his head. “I’m sure it’ll be fine. We’re not meeting her anywhere suspicious.” 

Remembering what they were doing, Claire tossed him her phone, “Here. Put in the address, we should get going.” 

Ten minutes later Claire was pulling into a trendy looking plaza area on the wealthier side of town. She nearly let out a groan when Jack pointed her in the direction of a fancy looking cafe with a weird french name she could never pronounce. She made a face as she pulled into a parking spot, regret already bubbling in her gut. 

“She seriously wanted to meet here?” she asked, not holding back her dismay. When Jack simply nodded she took another look at the cafe. “Dude, everyone in there looks like a Real Housewife. Are you sure they’ll even let us in?” 

Jack nodded again, still not catching on to Claire’s apprehension, “Yeah, I’ve been here before with Sam. They have good hot chocolate.” Before she could argue with him any further he started to get out of the car. With an eye roll, Claire reached out grabbing the sleeve of his sweater and pulled him back in. 

“Hold on. That’s it? You’re about to make a deal with a dangerous witch and you’re not even going to bring a weapon?” 

Jack huffed, “Claire, I told you this isn’t going to be dangerous.” 

“Yeah well better safe than sorry.” She pulled out her gun from her glove compartment and stuffed it in the waistband of her pants. Then covered it from view with her flannel, ignoring the way Jack was watching her with frown. 

“Even if it was dangerous, which it isn’t,  _ I  _ don’t need a weapon,” he proudly lifted his chin. Claire rolled her eyes and got out of the car wanting to get this over with as soon as possible. 

The pair walked into the cafe with Jack boldly leading and Claire cautiously trailing behind. It took everything in her power to ignore the disdainful looks thrown their way and not flip off every person in here. 

“Can I help you?” the hostess asked as if the two rugged kids wandered in here by mistake. 

“Yes please, we’re meeting someone here,” Jack asked with every bit of politeness Claire was certain she could never muster. 

“Name?”

“Rowena.” 

The woman hummed, dragging her finger down her list of names, She raised her eyebrows when she found what she was looking for. “Ah yes, she has already been seated. You can go on ahead.”

Jack thanked her and walked further into the restaurant. Meanwhile, Claire’s brain fixated on the name the nephilim said. It was a name she remembered hearing years ago, not long after she was reunited with the angel that wore her father’s face. Sam and Cas talked about her when they thought she wasn’t paying attention. And if her memory served her right they did not regard her in a positive light. 

She once again tugged on Jack’s sleeve, “Rowena? Isn’t she evil?”

“What? No.” Jack said firmly then shrugged her off. 

Claire, suddenly on high alert, did a scan of the restaurant. Her eyes immediately focused on a woman with flaming red hair. The young hunter had never met Rowena before, but she knew for certain that was her. Subtly clearly wasn’t the witch’s style as she somehow managed to stand out yet perfectly fit into the atmosphere of the cafe. The way she comfortably wore her purple ballroom gown made her look like the most expensive person in the room. If that wasn’t a dead giveaway that she was the witch, then the black cloak she proudly wore draped on her shoulders was. Blending in was clearly the last worry on her mind. 

Just as she assumed, Jack walked in a direct line to where she was seated in the back. Rowena smiled when she saw the nephilim.

“Jack, my dear,” she sang dreamily, reaching out for him with grabby hands. 

“Auntie Rowena!” the nephilim greeted cheerfully, holding her hands in return and giving them a squeeze. 

“Auntie?” Claire couldn’t stop herself from asking, she was taken aback by their apparent familiarity. 

“Oh, she’s not really my aunt,” Jack told her as if that was the reason Claire was surprised. “She told me to call her that.” He took a seat directly across from the witch, Claire followed and hesitantly sat down next to Jack. 

“I didn’t realize that you would be bringing a friend,” the witch said as if she just noticed Claire. 

“Oh, my bad, “ Jack apologized, “This is Claire Novak.” 

Rowena studied her carefully, “Let me guess, you’re the daughter of James Novak, the current vessel of a certain angel.” 

Claire’s stare hardened at the mention of her father, “How did you…” her sentence fell short as she suddenly felt exposed.

“I know  _ everything  _ dearie,” she said with a wicked smile. Then she took a long sip from a tea cup that was sitting in front of her with her pinky pointed up. Claire swallowed, suddenly feeling more nervous then when she walked in. Unfortunately, it was clear that Jack was feeling the exact opposite. 

“I remember how much you enjoyed the hot chocolate here, so I went ahead and ordered you one,” she said sweetly, pushing a mug towards Jack. She gave Claire a quick look that read that this was a courtesy that only extended to the nephilim. Claire on the other hand felt zero envy and was instead inspecting the suspicious mug from afar. Something about it was a little too… neat. From the perfect swirl of whipped cream to the even number of marshmallows. 

“Thank you!” Jack said happily, taking a sip of hot chocolate before Claire could stop him. Internally she cursed herself for not giving him a lecture about accepting food from witches before they came in. She relaxed slightly when he didn’t immediately die or get sick, but from that point she vowed to keep her guard on high alert or the both of them. 

“So, how are things back at the Bunker?” Rowena asked politely. 

“Everything is good,” Jack answered honestly. “No one is dying for once, and that’s… good.”

“And you’re not just saying that to please me?” 

“No, this time we’re being honest,” Jack gave her smile that read that they were referring to something that Claire didn’t understand. 

“Enough small talk. We came here for a reason, so tell us if you fulfilled your end,” Claire demanded. She was feeling uncomfortable watching Jack and Rowena acting like old friends having brunch, Claire just wanted to get what they came for and get the hell out of here. 

Rowena narrowed her eyes at the hunter and plastered on a fake smile, “I forgot my manners, please help yourself to a sweet treat. The strawberry tarts are my personal favorite.” She pushed the plate of pastries directly towards Claire.  _ Oh hell no.  _ There was no way those weren’t poisoned going by the way the witch’s eyes were practically begging for Claire to take a bite of one. 

“No thanks, I’m not hungry,” she gritted out, putting on an equally sarcastic smile. 

Jack, as oblivious as ever, helped himself to a blueberry muffin and Claire had been too distracted by her staring contest to stop the boy from taking a huge bite. Outraged by his lack of mindfulness, she socked his arm causing him to flinch and hold his arm with a pout. 

“What?” he asked, mouth still filled with muffin. 

“Dude, when an evil witch offers you sweets, you don’t shove it in your mouth first chance you get! Haven’t you heard of Hansel and Gretel?” 

Jack shook his head with a confused look. 

“I am offended by these accusations,” Rowena said dramatically. “I believe that I have long earned a bit of trust.” 

Jack swallowed his bit of muffin in one large gulp. “I trust you,” he told her, eyes shining with naive honesty. Claire couldn’t stop herself from groaning. “Claire still thinks you’re evil. She didn’t believe me when I told her you weren’t, but it’s not her fault. She doesn’t trust people easily.” 

“Oh my god…” she muttered, annoyed by the fact that Jack so openly exposed her. 

“I will not deny it. ‘Evil bitch’ is a term I’ve come to wear with great pride,” Rowena held her head up high. “Regardless of my many titles, I would never dream of hurting a hair on this boy’s wee head.” She leaned across the table and whipped off a blueberry smudged that had been on Jack’s cheek with her thumb as if it were further proof of her statement. Jack simply smiled and allowed himself to be dotted on by the witch as if he was a toddler and she were his actual aunt. 

“Yeah right,” Claire snapped, feeling so tired of watching this bullshit display. “You really expect me to believe that you would never take advantage of Jack’s innocence and you came all the way out to fucking Kansas out of the goodness of your heart.” 

“Yes because it’s the truth. I wasn’t exactly in the area when Jack called, but I would do anything for this darling boy,” Rowena gave him a smile that Claire couldn’t quite read, but it was definitely more real than any look she’d given her. 

“Sorry, I’m not buying it,” Claire crossed her arms, “You witches always have an ulterior motive.” 

“I have nothing to prove to you dearie, but if I must, I could provide an explanation,” the red head sighed and took another sip from her tea cup. “When you’ve lived as long as I have you learn a thing or two when it comes to self preservation. I’ve learned that it’s best to be on good terms with whoever is on top. Now, Jack is one of the most powerful beings in the universe next to God himself and it would be in my best interest to not make him angry. The same goes for the Winchesters. Although, I will admit that over time I’ve grown quite fond of the boy.” 

“See?” Jack said with an ‘I told you so’ look.

“Fine,” she rolled her eyes in return. “I’ll believe that you don’t want to be turned into a pile of dust.” Her self preservation shtick seemed believable enough, but that didn’t mean Claire would trust her. Witches were tricky and she could still try to screw them over. While Jack could probably turn her into dirt in a blink of an eye that didn’t mean he could beat her in a battle of wits.

“Like I said, I have nothing to prove to you. All that matters is that I have Jack’s trust.” 

“By the way, did you bring the spell?” Jack asked eagerly, finally bringing up their purpose of coming here. 

“Of course I did,” Rowena answered with a smirk. She reached into her purse and pulled out a vile with dark pink liquid swirling inside. “One love potion, just as you requested. Pour one drop into each party's morning coffee and they will instantly fall for each other.”

“Cool,” Jack made to grab the vial when Rowena suddenly pulled it out of reach. 

“Wait. Love potion is powerful magic. I couldn’t possibly just give it to you,” Claire sighed she knew there was no way it could be that easy. Rowena probably wanted to make a deal and Claire needed to make sure Jack didn’t get screwed over. “First, you need to tell me what you’re using it for,” Rowena demanded. 

“Um…” Jack’s mind blanked. 

“Don’t think I didn’t notice that you brought blondie here instead of one of your guardians. I can only assume that they don’t know we’re meeting?” the witch gave him a knowing look. 

“T-they know I’m here…” the nephilim stammered. 

“Really?” she narrowed her gaze as if she could read through all of his lies. “So you wouldn’t mind if I mention our little meeting to Sammuel next time he calls?”

“Okay fine, they don’t know,” Jack confessed. “But, I promise we’re not doing anything bad. It’s a good thing really…” 

“If it’s a good thing, then you wouldn’t mind telling me.” 

Claire could practically feel the boy trembling in his seat. She knew that he was seconds from breaking, so she tried to intervene, “It’s actually a funny story, we’re tryin -”

Unfortunately she was too late.

“We’re trying to get Dean and Cas together! I didn’t even know that they liked each other in that way until Claire told me and since then I’ve been paying more attention and I think she’s right! I just really want them to be happy and I think if they got together they would make each other happy. But they’re so used to being sad that I don’t think they would admit their feelings on their own. Which is why we need to help them.” Jack’s explanation came out as one big ramble with him hardly pausing to breathe. Claire’s jaw dropped, surprised by his sudden honesty she couldn’t even think to reprimand him for giving away their plan so easily. 

Even Rowena seemed to be surprised by his outburst, she sat there with a hand over her chest. “Why didn’t you tell me?! I would’ve helped a lot sooner. I’m just as sick of watching those two dumbbell’s dancing around each other as the rest of you! Why else do you think I always flirt with Castiel? I was hoping to get some kind of reaction out of somebody.” 

“W-we weren’t sure what you would say,” Jack replied shyly. 

Rowena straightened up in her chair, looking excited, “Well the first thing I would have said is that a love potion is not the spell you’re looking for. A love potion is for when you want two people to fall in love that don’t love each other. Dean and Castiel are already smitten which means the love potion is useless. You need something to force them to admit their feelings. Something to loosen their lips one might say.”

“You mean like alcohol?” Claire scoffed.

“Almost, except I find truth serum to be far more dependable,” she said with a mischievous grin. 

“And you have that?” Jack's eyes lit up.

“Not on me right now, but I can bring it to you in a couple of days.”

“What’s your price?” Claire crossed her arms waiting for the catch, there always was one. 

“No price. Just count it as my contribution towards a worthy cause,” she waved her hand. 

“Seriously?” Claire raised her eyebrows in disbelief. 

“Seriously. I’ll just add it on to the Winchester’s never ending tab of times they owe me,” she said with a dramatic eye roll that made Jack giggle. 

After that, Jack chugged the rest of his hot chocolate while Rowena promised to deliver the potion to the Bunker herself in a few days. The nephilim thanked her for her help and the hot chocolate with a big hug. The witch looked slightly uncomfortable for a second before ultimately returning the hug. While Claire would admit she misjudged the witch, she was not about to hug her. Instead she opted for an awkward smile and slight nod of the head before turning to leave. 

Once they were back in Claire’s car and driving back to the Bunker, Jack was staring at her with an ‘I told you so’ grin on his face.

“So…”

“So, what?” Claire gave him a look. 

“I was right,” Jack announced proudly. “I knew that Rowena would help us and that she was trustworthy.” 

Claire rolled her eyes and thought that he was being childish, “Fine, I’ll admit that she was alright and not the evil witch I had pictured in my head. But, I will not apologize for being cautious.” 

“Either way, Rowena is way better than that Sean guy. Which means I’m a better judge of character than you thought,” the nephilim beamed with pride. 

“Whatever,” Claire groaned, not willing to give him the satisfaction, “I still think your whole ‘Auntie Rowena’ thing was freakin’ weird.” 

Jack shrugged, “I mean she is kinda like my Aunt. She’s at the Bunker pretty often and she always pinches my cheeks.” 

“Has anyone ever told you that your family is really weird,” she teased. 

“Yeah,” he said honestly, “but it’s all I’ve ever known and I don’t think it’s that weird. I mean they’re no weirder than your family.” He gave her a playful nudge. 

“True…” she sighed looking at the road in front of her. 

Jack’s phone made a noise and he pulled it out of his pocket. “Awesome! Dean’s making homemade burgers for dinner tonight,” he paused for a moment, looking at her before making a decision, “Do you want to have dinner with us? Dean’s burgers are really good and he rarely ever makes them.” 

“I probably shouldn’t…” she said automatically. She didn’t even know why she said it. It’s not like she had anything else planned that night besides driving back to Sioux Falls and getting the cheapest fast food she could find once she hit the three hour mark. Her life of solitude made rejecting social invitations second nature. 

“Don’t worry, Dean always makes extra. We eat a lot and whatever we don’t finish he freezes for later. He also makes one for Cas even though he doesn’t always eat it. So, it’s no big deal if you come. Please, it’ll be fun,” he looked at her with pleading blue eyes and Claire felt guilty. Saying no to him would feel like kicking a puppy. 

“Alright. Fine, I’ll go or whatever,” she said without really thinking about it. She just couldn’t seem to justify rejecting the offer. Either way, her reluctant agreement surprised even herself. Maybe she did it for Jack or maybe she did it to prove Alex wrong for every time she called her an antisocial loner. But what mattered is that she did it. 

She could practically hear Alex’s voice in her head say, “they don’t count,” and she found herself agreeing. Castiel, Jack, and the Winchesters were less like peers and more like distant family. They felt like three dorky uncles and an equally dorky cousin. Still, hanging out with them not under the guise of a hunt seemed like a step in the right direction. 

She was a self trained introvert, something that had been formed out of necessity rather than desire. She wasn’t like this when she was a kid. Between school, church, and Girl Scouts she had obtained quite a large group of friends. It seemed like her family had plans every weekend which was a lot at the young age of twelve. That Claire was gone now and she knew better than to let people get too close.

All she had now was her strange hunter family and the decision to let them in was not one she made intentionally. She didn’t find them, they found her. They wormed their way into her heart without consent and now that they were there they wouldn’t leave. 

But with the reminder that everything is temporary hanging over her head, she often tried distancing herself from them too. As if it were her destiny to be alone. Which is why she was shocked she agreed despite every instinct begging her to say no. 

It wasn’t until she was driving back to Sioux Falls that she let herself admit she was happy with her decision. Even if it cost her to not make it back to Jody’s until 2:00 a.m. 

Jack was right, the burgers had been delicious. She hadn’t had a proper one ever since Alex decided to be vegan. Since then the only patties in the Sheriff’s freezer were made from beyond meat. Although she liked them more than she cared to admit, the taste wasn’t the same as a real burger no matter what the packaging claimed. She even convinced herself to have a second one, once she saw Dean eat his third and Jack finish his second. 

Besides the food, her company had also made it an enjoyable experience. Her and Dean argued for an hour about the best movies of the 80s, she talked to Sam about books and found herself genuinely interested, and throughout the dinner she would nudge Jack under the table any time she caught Dean and Cas staring at each other for an abnormal length of time. It was refreshing to have a conversation with them that wasn’t about hunting. In that moment they could pretend that they were normal people with few worries, it was the mental break Claire didn’t realize she needed. 

_ This is only temporary. _

Claire’s inner voice reminded her once it noticed her feeling far too comfortable. However, for the first time it didn’t make her want to distance herself. If this was truly only momentary, she wanted to enjoy the time they had together, no matter how short it may be. 

  
  
  
  
  
  


**Notes for the Chapter:**

> I hope you enjoyed a little bit of Claire POV. I felt like it was necessary since the last few chapters have been mainly Jack. Thank you to everyone who has been following this story so far. It warms my heart to hear that you guys have been enjoying it :)


	9. Chapter 9

**Notes for the Chapter:**

> Hello I'm back! Sorry it took so long lowkey my posting caught up with how far I wrote. To make up for it, here is an extra long chapter! Don't worry this story isn't abandoned I am just slow. Thank you for all your comments they inspire me to write faster!

Rowena came to him four days later. She didn’t even tell Jack that she was coming. One day he heard a knock on his bedroom door and when he opened it he was surprised to find the witch standing on the other side. 

“I brought the serum,” she said excitedly, closing the door behind her. “Here. Keep it safe. I don’t want to have to go through the trouble of making it again,” she pushed a small vial into the palm of his hand.

“Thank you,” he told her and looked down at the small glass in his hand. “How do I use it?” 

“Put a drop in both Dean and Castiel’s morning brew and they’ll be spilling their guts in no time. The spell only lasts three hours, so make sure they talk quickly,” the witch explained. 

“Won’t they eventually realize that they are under a spell? What if they figure out it was me?” Jack worried. Dean and Cas were smart. There was no way they wouldn’t notice, especially once they started to say things they didn’t mean to say aloud. Then they would become suspicious and it wasn’t like there were a lot of people that lived in the Bunker. Even if the coffee came from a shop it wasn’t like their local barista had a good motive for poisoning their drinks.

“Don’t worry dear, I’ve planned it all out,” she said, giving his left cheek a pinch making him wrinkle his nose in bewilderment. “Tell Dean and Cas you’re going on a hunt for a witch named Angela Dealy in Arkansas. She has quite the history of playing tricks on men who’ve wronged her. Just plant the serum midway through the hunt and they will naturally assume it was her. Then they will call me and I will tell them to simply wait until the spell wears off.”

Jack furrowed his brow as he went over the plan in his head, “But, they might end up killing her. Are you sure she deserves it?”

“Does she deserve it? Oh course she bloody does!” the ginger snapped. She took a moment to regain her composure before explaining, “let’s just say that Angela has been a thorn in my side for quite some time. Consider it as your payment for my services. Besides, she’s always causing trouble. Do some research and I’m sure you’ll find something on her.” 

That night Jack did research Angela Dealy and he discovered that Rowena had not been lying. That area had quite the history of strange deaths within the past ten years and all of them had been young men with a connection to Angela. All except one woman, Cassidy Jackson, who had died three weeks ago. Jack wouldn’t have considered her until he learned that her fiance had already moved on. According to his Facebook page he was now dating Angela Dealy herself. That was an abnormally short amount of time for a man who was most likely still grieving, especially since his ex fiance’s death had been strangely sudden. According to the autopsy report she died from heart failure. This sounded natural until you consider that she was a young adult with no preexisting conditions. Especially for someone as active as Cassidy had been, he learned from a picture of her after running a marathon last year.

Unfortunately, Jack couldn’t find any proof that Angela was a witch, but hopefully the deaths would be enough reason for Dean and Cas to take the case. That only meant that Jack would have to go into this case pretending as if he knew less. 

Soon after, he called Claire up to tell her about the plan. To his relief, she gave her approval, sounding impressed by the witch’s ideas. 

“There’s only one problem,” Claire rang out from his phone’s speaker. “We need to get Sammuel out of the house, so that he doesn’t go on the hunt.” 

“Why?” Jack had just assumed that Sam would come along. Most of the time the four of them hunted as a family and any other time they hunted in pairs. It would be odd if only Sam was left out of this hunt.

“Isn’t it obvious? Last time, our plan would have worked if Sam didn’t interrupt. We can’t have him messing it up this time, especially since you only have three hours.” 

_ She’s right.  _ He just didn’t know how they could leave Sam out of the case. Normally, he would offer to go with Sam on a different hunt, but Jack needed to be with Dean and Cas in order for it to work. “How? Sam always comes with us on hunts and it’s not like I can force him to not go,” Jack said, falling back on his bed with a sigh. 

“Leave it to me,” Claire promised. “Just tell Dean and Cas about the case and I’ll make sure the moose is occupied.” 

  
  


He decided to wait until the following morning to bring up the case. Sam left early for his daily jog which left a small window of time when he was alone with Dean and Cas. It was perfect.

Jack walked into the kitchen with his laptop open and was thankful to find Dean and Cas already in there. He had been counting on the fact that Cas doesn’t sleep and Dean woke up early most mornings. The only time he ever slept in was if he had been up drinking the night before. Castiel told him that the reason for this was because the Winchesters were inflicted by nightmares which meant that they could not sleep long before being brutally awakened by the terrors of their own mind. They were a result of all the horrible things they’ve witnessed in their past. Jack understood. He had nightmares sometimes too. It usually ended with him waking up drenched in sweat and feeling clammy. His hands would uncontrollably shake until he sought out Castiel for comfort. 

“Mornin’ kiddo,” Dean’s cheerful greeted interrupted his thoughts, “I made coffee and bacon. The breakfast of champions! Help yourself,” the eldest Winchester was leaning against the counter already taking a large bite out of a strip of bacon. 

Jack smiled in return and set down his laptop on the table at the spot across from where Castiel was sipping his own coffee. Then he walked over to where Dean gestured and stuck a piece of bacon between his teeth while he poured himself a cup of coffee with sugar. He held the bacon in his mouth until he took a seat in front of his laptop and finally ripped the bacon out of his mouth. He washed down the bite with a generous gulp of coffee and gave a content sigh at the warm feeling it left in his stomach. 

“I found us a case,” he finally spoke up, looking at both Dean and Cas expectantly.

“Nice,” Dean plopped down on the seat next to him, stuffing the rest of his bacon strip into his mouth. “Whatcha got for us?” Dean asked, his speech muffled by the bacon still in his mouth. 

Jack explained to them everything he found showing them the evidence on his laptop. He started with all of the strange deaths over the past ten years up to Cassidy Jackson’s recent death. Last he showed them Angela Dealy and introduced her as his number one suspect, leaving out the part where he knew she was indeed a witch. 

“Good job Jack,” Castiel told him with an encouraging smile when he finished. “You were able to spot a pattern between the deaths.” 

Dean grimaced. “Yeah… but I’m not sure it’s enough. I mean you’re definitely on to something, it just might not be enough to justify driving down there and killing this Angela chick just because she runs a goth Etsy shop.” 

“I’m not saying that we should kill her, she’s just a suspect. I’m saying that there is a clear pattern in the deaths and that’s worth checking out,” he argued. Jack thought he’d gathered enough evidence that he didn’t even consider the possibility of Dean rejecting the case. He internally cursed Rowena for not giving him enough information to go off of. 

“I wouldn’t necessarily call it a ‘clear’ pattern. They all look like normal deaths, it could just be a coincidence. And even if they are related I’m not sure that Cassidy fits the pattern since she’s a girl. Heart failure is unusual for someone her age, but it’s not impossible. You have to also take into account her eating habits, family history -” 

“Dean…” Castiel sternly interrupted. The angel glanced at Jack then back at Dean, giving him a look the nephilim couldn’t decipher. 

Dean let out a sigh then looked back at Jack with an encouraging smile, “You know what? Checking it out won’t hurt anybody. I can tell that you worked really hard on this and it’s not like we had anything else planned today.” 

“Cool,” Jack smiled back at him. He knew that Dean only agreed to the case to humor him. Normally, Jack would be offended by the lack of faith he had in him, but frankly he was just glad Dean didn’ t say no. 

They sat in a comfortable silence for the next few moments. The only sound that could be heard was the clicking from Jack’s laptop, as he tried to find more information against the witch, and the occasional slurp from Dean drinking coffee. Until it was interrupted by Sam making his way into the kitchen, covered in sweat from his jog. 

“Dude, seriously? Couldn’t you have showered before going in here? You smell like shit,” Dean blanched. 

“It’s called the smell of hard work, Dean. Clearly it’s something you wouldn’t know,” Sam teased, leaning against the counter and taking a sip from a water bottle. 

“Yeah, well if it smells like that then I don’t want to know. Seriously, I could smell you before you even walked in the room.”

Sam ignored his brother’s comment and instead took in the food on the counter with a huff, “Coffee and bacon? For breakfast? Really Dean, that’s the best you can do?” 

“What’s wrong with it?” Dean shrugged. He held up his cup of coffee for Sam to see, “I got caffeine to wake me up and protein to keep me going.” 

“You know that the majority of bacon is fat and cholesterol right?” As Sam talked he pulled out the ingredients to make his daily protein shake. “And you let Jack eat it too. You know that you’re bad parents.’

“You say that as if you’re not a part of this. The way he turns out is just as much your fault as it is ours.” Jack paused looking up from his research to wonder whether he should be offended or not. As if he read his mind Cas shook his head with an eye roll in Sam and Dean’s direction. Jack shrugged it off as just another one of the brother’s arguments. “Besides, I -“ 

Dean was interrupted by the loud shriek of the blender and Sam who stood next to it with a triumphant smirk. Dean returned with a fake laugh as he flipped off his little brother. 

When the blender stopped, Dean continued, “Anyway, before I was rudely interrupted I was going to tell you that we’re going to check out a case later in Arkansas. Wanna come?” 

Sam sucked in a breath. “I can’t. When I was jogging Donna called and asked if I could help her hunt down a rugaru. I told her I would go.” 

“Is she in trouble? Do you need extra help?” Dean asked. 

“Nah, I think we got it covered,” Sam took a long sip from his smoothie, “But I don’t think she’d object to extra hands, if you want to split up. I can take Jack, I don’t think he’s ever hunted a rugaru before.” 

“No!” Jack said quickly, feeling slightly panicked, “I want to go with Dean and Cas.” 

“Why not? I thought you liked Donna. She’s the police officer that gave you candy from her desk, remember?” Sam said looking at him funny. 

“I-I do. I do like her,” he said slowly trying to think of a good reason for his mini outburst. “It’s just - “ 

Thankfully, Dean swooped in to save him, “Jack was the one who found us the case, so I think he wants to see it through. If it turns out to be nothing, maybe we’ll drive up and help out you and ole’ D-Train.” 

To the nephilim’s relief Sam merely shrugged it off, “That’s fine. Like I said I think Donna and I got it covered. Whoever is finished first can join the others and if not will meet back here in a couple days.” 

  
  
  


Jack had hoped that he could relax once they were on the road towards the hunt, but hours later he found himself sitting on the edge of a motel bed, feeling more nervous than before. The source of his stress was the small vial wrapped in a pair of socks in the bottom of his backpack that had been burning a hole in the back of his mind since he arrived. Thank goodness this wasn’t exactly a real hunt because he was currently too distracted to think straight. 

Jack's thoughts were interrupted by Dean storming into the motel room with a bag of fast food in one hand and his phone in the other. “Alright fellas,” Dean announced, tossing the bag onto the table and facing them, “So I rang Rowena, I figured if it turns out this Angela chick really is a witch then she might be able to tell us something. Turns out Jack was right. Angela Dealy is definitely a witch and for whatever reason Rowena doesn’t not like her. According to her, killing an innocent girl to get with her fiance is something Angela would do.”

“But we can’t just pretend that Rowena isn’t the type of person to hold a grudge,” Castiel pointed out. 

“Exactly. Which means we still need to do some investigating. We need to head down to the station and get the autopsy report for Cassidy Fisher and any information we can on the other guys that died. We should also talk to some of her family, friends, and probably the fiance, Derek. We have to be careful about that one because he might alert Angela that we’re snooping.” 

“We should also consider the possibility that Derek might be under a spell. He did move on from Cassidy a lot faster then someone who should be grieving would,” the angel added. 

“Damn, you’re right. I didn’t think of that,” Dean sighed rubbing his forehead. “And after that we still have to decide what to do with her. If we think she’s dangerous, we might have to kill her; and if we decide she’s just boy crazy, then we’ll have to find a way to arrest her.” 

“You mean plant evidence to suggest she killed Cassidy?” Castiel asked. 

“Pretty much. Which means we’ll have to deal with legality shit and then we’ll need Sam. Then, we’ll just have to pray she doesn’t break out or we’ll have a pissed off witch on our hands,” Dean pulled out a beer from the mini fridge and plopped on a chair. “Man, this case is going to be a lot more work than I thought.” 

Jack slightly relaxed realizing that the longer the case the more opportunities he would have to enact his plan. Dean stood up muttering something about calling Sam before walking outside. Jack dropped backwards on to the motel bed and pulled out his phone to text Claire. He asked her for advice about when it would be a good time to use the truth serum. She said to wait until they’ve snooped around enough to potentially catch Angela Dealy’s attention. Thinking back to what Dean said he decided to do it after they talked to Derek. It was believable enough that he would tell her that “FBI” agents came to ask him questions about Cassidy’s death. Any intelligent witch would quickly notice that was the obvious hunter disguise. 

“You should eat something,” Castiel said suddenly referring to the bag of fast food Dean brought in. 

“Oh,” Jack sat up furrowing his brow. He had totally forgotten about food, being too caught up in his text conversation with Claire. 

“That was a long car ride, you must be hungry. A stick of beef jerky is not a proper meal,” Cas reiterated knowingly. 

“Right..,” Jack said with a small smile. Putting his phone back in his pocket, he walked over to the bag and pulled out his burger. He unwrapped it and took a hesitant bite, fully aware of the angel’s gaze still on him. 

“Is there something on your mind Jack?” Cas asked suddenly. Jack nearly choked from surprise. “Lately, you’ve been a bit distant.” 

“No, there’s nothing.” 

Jack instantly felt a pang of guilt. He hated lying in general, but he especially hated it when it was lying to Cas. He’d never realized how much of his time was spent scheming with Claire. Apparently a lot of it considering that all he normally did was hunt or sort through the Men of Letters vast archives with Sam. 

Castiel stared at him for a second, clearing not swayed by Jack’s quick response. “Jack, you know that you can talk to me about anything.” 

“Yes, I know. I really do,” Jack told him sincerely. “And if there was something, I would tell you,” Jack added, trying his hardest to convey that there was no reason for the angel to worry. Because there wasn’t. No one was hurt or in danger and all of his efforts will be for the better. 

“Okay,” Cas replied. He still looked a little suspicious but subdued for now. 

  
  
  


Jack anxiously bounced his leg as the stiff, itchy fabric of his suit pants were making him feel uncomfortable. It was either that or the fact that he was stuck sitting on a hard plastic chair in the middle of a cold, overcrowded police station.

Earlier that morning, Dean had suggested that they would get more work done if they split up. He had given Jack the choice of either going with him to interview the victim’s family or going down to the station with Cas. He almost chose to go with Dean, since he knew that the family would give more information than the police ever could, but after his conversation with Castiel yesterday, he decided to go with him instead. Even if that meant sitting on an uncomfortable chair waiting for Castiel to come out of the detective’s office with Cassidy’s file. He would have gone in with Cas, but the detective took one look at Jack and decided that he was a rookie and therefore could not be trusted with such sensitive information. 

Jack was absentmindedly tapping his fingers on the bottom of the chair when Cas finally came out with the file in hand. Jack quickly stood up, “Did you find anything?” he asked eagerly. Cas cocked his head and led them to a corner of the room far away from any prying ears. 

“Cassidy Jackson did not die of heart failure,” he said shortly, opening up the file to show him. “When they did the autopsy they found that her heart was charred black. The doctors had never seen anything like it. Apparently, the reason they told the family that she died of heart failure is because technically, her heart did fail her.” 

“So that’s proof that she died from witchcraft, right?” Jack asked excitedly. 

“Not on its own. No,” Jack deflated a little, “That was until he told me they found a hex bag on her when she died. Of course the police didn’t know that was what it was, they assumed it was some type of devil worship. Cassidy came from a very religious family, so they figured it was best if they didn’t release that to the public, since they didn’t think it was relevant. Little did they know it was the direct cause of her death.”

“So it was a witch?” Jack repeated waiting for confirmation.

“Yes, Jack. It was a witch,” the angel confirmed with an amused smile. 

“Let’s go tell Dean!” Jack said excitedly before racing out of the police station. 

They gave Dean a called once they found a bench to sit on outside. The older Winchester had dropped them off there earlier meaning they were stuck until he came back. Jack kinda wished they had another car so that they could help Dean with whatever he was doing, but they always brought the Impala on long road trips. 

“ Hey Cas, you learn anything at the station? _ ”  _ Dean’s voice rang out through the phone speaker. 

“Cassidy was killed by a witch!” Jack answered for him.

“ Really? Are we sure? _ ”  _ Dean's question was clearly meant for Cas. 

“Yes. They found a hex bag in her pocket,” Castiel confirmed.

_ “ _ Welp, it sounds like you guys had better luck than me _.” _

“Why? What happened?” Cas said, looking slightly concerned.

“Nothing, but talking to Cassidy’s family was kinda a bust. I mean they believe that there was more to her death than heart failure, but it’s not like they had any proof that it wasn’t. I asked them if they noticed her acting weird leading up to her death, they said no. Then, I showed them a picture of Angela and they said they have never seen her before. Like I said, I didn’t learn jack,”  Dean’s voice sounded mildly irritated. 

“Where are you now?” 

_ “ _ I started trailing Derek. You know, to see if he does anything suspicious, but he hasn’t done much. I followed him from his house, but the only place he went to was some hipster coffee shop. I guess the style is a little edgy, but that’s about the only thing off about it. Most of the customers just look like college kids doing homework.” 

“Well, Jack and I are done at the police station. Can you pick us up?” 

Dean was silent on the other end for a moment,  “Uh… See the thing is, I’m afraid that if I leave, I’ll lose track of Derek. I think I’m going to keep trailing him. That way I can be sure he’s alone before I question him.” 

“Dean no. It's too dangerous,” Cas said angrily through the phone. “We were supposed to interview him together because talking to Derek could alert the witch. If you do it alone you could be trapped at her mercy without backup. It’s too soon anyway we just started the investigation.”

_ “ _ It is not too soon Cas! We know for a fact his girlfriend is a witch and that his ex fiance died from witchcraft. Sounds pretty cut and dry to me! I’ll be fine, I’m freakin’ professional!” 

“You don’t have a choice Dean!” Cas pinched the bridge of his nose frustrated. “You dropped us off. We’re stuck here until you pick us up!” 

“Not my problem Cas! Just get an uber!” 

“I don’t know what that is!” Cas practically yelled, until he looked down at the phone in his hands and groaned. “He hung up… “ the angel sighed sadly. He looked at Jack for a second and asked, “Do you know what that is?” When Jack shrugged and shook his head Castiel let out a disappointed huff. 

They sat on the bench for a while, Jack swinging his legs back and forth absentmindedly, until it became painfully obvious that Dean wasn’t coming. Jack unsuccessfully tried to look up what an “oobur” was, but the search results came up empty. Granted, he wasn’t exactly the best speller, especially when it came to words he’s never heard before. 

Castiel then suggested just walking back to the motel and Jack agreed. It wasn’t that far and he was willing to do whatever would get him out of the suit faster. Luckily, they didn’t get very far before a very friendly police officer offered to give them a ride. 

Finally back in the motel room, Jack was seated cross legged at the end of a bed watching Castiel anxiously pace back and forth across the length of the small room. 

_ “This is Dean’s other other phone. You know what to do…”  _ Jack heard Dean’s voicemail ring out for what must be about the twentieth time. At this point the sound had permanently etched itself into his brain. Castiel had started calling it from the moment they stepped into the motel room and Dean had yet to respond. 

“Dean. Call me. Now.” Castiel growled into the phone before aggressively pressing the red button. The more Jack watched Cas worry about Dean, the more nervous he started to feel himself. Earlier he thought Cas was just overreacting, afterall Dean was a“professional” just as he claimed. However, the more time that passed without any word from the eldest Winchester, the more concerning the situation was appearing. It was going on two hours since their call to him, that could be enough time for him to run into some trouble. 

“Should we look for him?” Jack suggested. At least, it would feel better than staying here waiting. Besides, if Dean was in danger, calling for backup might not be an option for him.

“No,” Cas said resoundingly, while looking like he wished he could do the exact opposite. “He could be anywhere in this town by now and we don’t have a means of transport. Also, we became far too familiar with the cops today that getting caught stealing a car would be a bad look for two FBI agents.”

“Then what are we going to do?” Jack asked in a small voice.

Castiel bit his bottom lip. “We’ll wait another hour then we look for him.” Jack nodded sadly.

“Is there something bothering you?” the angel asked him with a concerned look.

“It was my idea to come on this hunt. If something happens to Dean while we’re on it -”

“Then it wouldn’t be your fault,” Castiel finished for him. “Dean shouldn’t have gone off on his own. That was his dumb descion and it has nothing to do with you,” he said firmly with a hand on the young boy’s shoulder. Jack nodded that he understood, but that didn’t stop the thought from weighing on his mind. 

Luckily, that thought didn’t fester for too long as they finally heard the low rumble of the Impala pulling up a half hour later. Jack noticed the way Castiel’s whole body relaxed in relief at the sound. That didn’t stop the angel for rounding on Dean the moment he walked through the door. 

“Where the hell were you?” he growled in the hunter’s surprised face.

“Nice to see you too Cas,” Dean replied sarcastically.

“Dean,” Cas snapped, clearly not in the mood for jokes. 

“Relax, I was exactly where I said I was. I just talked to Derek for a bit, it wasn’t that big of a deal,” Dean said with an eye roll. 

“If that’s all you did, then why couldn’t you have bothered to pick up your phone?”

“Because you were calling me like crazy. Can’t have a nice conversation with my phone going off every five minutes, so I turned it on silent.”

“And when you were finished? You didn’t even think to check? Or send a message that you were coming back? For all we knew the witch could have found you.”

“I’m not a dumbass Cas! I waited until he was alone to talk to him. Besides, if Angela did show up I would’ve killed her before I’d let her close enough to slip anything in my pocket. In case you forgot, I’ve been hunting monsters since I was big enough to hold a gun! Plus, I didn’t text you cause I knew you’d be pissed at me for doing it.” 

“This isn’t just about you Dean,” Cas grumbled. “You abandoned us back at that station. The least you could have done was made sure we made it back to the motel. What if something had happened? Sometimes it seems like you don’t even care!”

“Oh excuse me, for assuming that a freakin’ warrior of God could take care of himself,” Dean scoffed. 

Meanwhile, Jack was pivoting his head back and forth between the two as if he was watching a tennis match. Whenever Dean and Cas fought like this, Sam would always joke that they were like an “old married couple.” Jack never really understood what that meant, surely old married couples weren’t this… aggressive. That thought made him suddenly miss the younger Winchester’s presence. He always knew how to break up Dean and Cas’ arguments, usually by interrupting or changing the subject. Jack wished he had this ability, but unfortunately he was a lot more socially inept than Sam. 

“So, did you learn anything from your talk with Derek?” Jack tried his best. He really did. And he almost believed that he had said the right thing when he saw the way Dean’s face lit up at his question. That was until he noticed the sharp glare Castiel was sending him. 

“I am so glad you asked that Jack, because as it turns out, I learned quite a bit from our conversation,” Dean looked at Cas with a shit-eating-grin causing the angel’s frown to deepen. “For starters, I am almost certain that Derek is under a love spell. I mean, when I asked him about Cassidy, he seemed way too nonchalant for someone who just tragically lost his fiance. Believe me, I’ve talked to a shit ton of people in mourning throughout the years and that was not him. Then, when I mentioned Angela it was like his whole demeanor changed. Seriously, I could not get him to shut up about how great she is. That was until I asked him if Angela ever had anything against Cassidy, then bam! Suddenly, he became super defensive and angry at me. Which is how our conversation ended with him cussing me out of his house. So yeah, he showed all the signs of a love spell.” 

Castiel crossed his arms and raised an eyebrow, “Or maybe he played a part in Cassidy’s death. Maybe, he never truly loved Cassidy, it could explain why he wasn't upset. Derek could have seen this as an opportunity to get rid of her, so that he would be free to be with Angela.” 

Dean shook his head, “That’s a fair point, but when I talked to Cassidy’s family they kept going on about how in love the two of them were. They even said that Derek was a broken wreck the first few days after her death, then suddenly he changed. He started acting as if nothing happened. They just assumed it was a weird coping mechanism. Mood swings, sudden change of behavior, sounds like a love spell to me.” 

Castiel sighed. “Alright fine. What’s our next steps?”

“Now, here comes the hard part. We have to decide if Angela’s worth ganking or not.”

“How do we do that?” Jack asked, curious. 

“We watch her. See if this is a one and done or if she’s going to try again,” Dean told him. “Which can get a little tricky, since we don’t want to get caught. So, make sure you're wearing your best civilian clothes, kid, we’re going to have to do some blending.”

“You know where to find her?” Jack asked, surprised.

“Yep, Derek was very willing to give me information until I pissed him off. Apparently, she works at the hipster coffee shop I followed Derek to. That’s why he stuck around for as long as he did, he was trying to ‘spend time’ with her while she worked. We might have to wait till tomorrow morning cause she works the early shift.” 

A big lightbulb went off inside of Jack’s head. This was the oppurtunity that he had been waiting for. The one that Rowena had anticipated. She did keep telling him to pour it in their morning coffee, she must have said this knowing that Angela Dealy worked at a coffee shop. This was the perfect time to do it since Dean already talked to Derek. It was completely plausible that he would tell Angela that the FBI had questioned him about Cassidy’s death and that in response she would try to sabotage their hunt. Sabotage their hunt by spiking their drinks with a spell. It sounded reasonable enough to Jack, all he needed to do now was enact the plan. 

  
  
  


The next day the trio entered the dark coffee shop. According to Dean, their plan was to just pretend to be normal customers and keep an eye on Angela Dealy. They wore their normal clothes and kept their FBI badges hidden away inside of the Impala’s glove compartment. 

Jack spotted Angela Dealy immediately recognizing her from her social media photos, her strikingly pale bleach blonde hair was hard to miss. His nerves had been skyrocketing ever since he left the motel room. His sweaty palm was currently wrapped tight around the truth serum vial concealed by his jacket pocket. Today was the day he would finally use it. He only had one chance to not mess this up meaning the pressure was on big time. 

“Cas and I are going to find a lowkey table, you go order the drinks,” Dean told him, pulling a twenty dollar bill out of his wallet. 

“W-why?” Jack stuttered. Truthfully he hadn’t been paying too close attention to what Dean said, too focused on coming up with a plan in his head. 

“Because this place is mostly filled with young kids, meaning Cas and I stick out like sore thumbs and we do not want that. You on the other hand blend right in, so you’re going to have to take one for the team.” Jack nodded slowly, taking the bill from Dean’s hand. He took a deep breath. This was good news actually. If he was the one to pick up the drinks then it would make it a lot easier for him to pour in the truth serum without drawing Dean and Cas’ attention. “Get me a red eye will you?” Dean finished giving him a reassuring pat on his arm. 

“Do you want anything Cas?” Jack asked. 

The angel shook his head, “No, I’m fine.” The nephilim internally cursed, this definitely put a dent in his plan. Castiel getting a drink was crucial and he felt a little angry that he hadn’t anticipated it before. After all, Castiel only ever ate or drank anything when he felt like being included. 

He nervously walked up to the register where Angela Dealy herself stood. He quickly scraped together a new plan in his head and crossed his fingers that it would work. “Hi, can I get a red eye and a black coffee,” he said, purposely telling her Cas’ usual order instead of his own.

The witch smirked, “Heavy coffee drinker, aren’t ya? Must’ve had a late night.” 

“You could say that,” he said letting out a nervous laugh. 

Angela raised her eyebrows at him before continuing to type on her register, “That’ll be $7.50.”

He handed her the twenty and released a breath he hadn’t realized he was holding. Thankfully, she didn’t try talking to him again. Except for when she asked for his name and he accidentally gave her his real one. He dug his hands deep in his pockets, one hand still tightly clutching the vial while the other held Dean’s change, as he stood amongst the other young adults waiting for their coffee. 

After he heard them call out his name, he grabbed the drinks and stole a glance towards Dean and Cas. To his relief, they looked like they were in the middle of a serious conversation. Taking the opportunity, he swiftly made his way to the table in the corner that was aligned with napkins, sugar, and creamer. He took one last scan around him before taking the vial out of his pocket. He carefully lifted both lids and poured a drop into each one just as Rowena instructed. Once it was done Jack felt a pang of guilt for tricking the two people he was closest to. He quickly brushed off that thought. He was too far in, there was no going back now. 

He plastered a smile to his face as he walked back to their table. “Here you go!” he said cheerfully, placing Dean’s cup in front of him. 

“Awesome!” Dean exclaimed, immediately taking a sip. 

Jack then turned to the angel, “Um, they messed up my order and gave me the wrong drink. Do you want it? I’m not a big fan of black coffee and I know you drink it sometimes. So, why waste it?” He ended with a nervous laugh, fingers crossed that Cas would take it. 

“Sure,” Cas accepted with a small smile. 

“Dumbass witch can memorize an entire book of spells, but she can’t get a freakin’ coffee order right!” Dean said suddenly. “Go ahead and buy yourself another one with my change. If she screws it up again we might have to fight her now because that is all the cash I have left.” Jack’s eyes widened slightly, surprised by how quickly the potion worked. 

As he waited in line he watched Dean and Cas out of the corner of his eye. The moment he saw Cas finally take a sip, he whipped out his phone and set a timer for three hours. That would mark how long he had to get them to talk about their feelings. 

“Back already? I think you’ve had enough caffeine kid,” Angela said with a smirk when it was his turn. 

“A hot mocha please,” Jack said ignoring her comment. He would prefer to speak to the witch as little as possible. He did not want to draw too much attention towards himself and the fact that she already remembered his face was unsettling enough. 

“After that red eye, I would think you’d want decaf. Skinny kid like you might have a heart attack from too much coffee,” she tried again to make conversation.

“It wasn’t for me,” Jack mumbled. 

“Tough crowd,” she sighed, giving up. 

As he waited for his drink, he watched Dean and Cas from the other side of the room. They were back to having a serious conversation. Jack hoped that they were talking about their relationship and not the case. That would definitely make things a lot easier for him if they got that conversation over with without him having to intervene. 

Feeling eager to get to Dean and Cas, Jack had planned to quickly grab his drink and return straight to his table once his name was called. Which is why he was startled when a hand grabbed his wrist the moment he touched his cup. His head whipped up and his eyes widened when he saw that it was none other than Angela Dealy. 

“Hey jitters, I saw you put something in your friends’ drinks.” 

“I-I didn’t -” Jack tried denying. 

“It’s okay, I won't tell,” she said with a playful smile. “I wanted to thank you, actually. Your little trick is just the distraction I needed to skip town without the hunters noticing.” 

“H-how did you know they were hunters?” he asked the first thought he had.

“The flannel, the machizmo, the stiff in the three piece suit. It’s painfully obvious. That, and my boyfriend told me an FBI agent was sniffing around asking him questions yesterday. Your friend fits his description to a tee,” she said with an eye roll. She clearly had a distaste towards hunters. 

Jack was left gaping like a fish, unsure of how to respond. 

“It’s okay, you don’t have to say anything,” she gave his hand a pat. “I don’t even care about why you did it. Just wanted to say thank you.” She gave him a wink before walking away. 

The nephilim felt like he could throw up. He ruined the case. The witch was getting away. Cassidy’s death would never be avenged and it was his fault. Dean and Cas won’t be able to work the case while they're under the truth spell. He had unknowingly given a murderer a three hour head start. All for his own selfish reasons. 

He shook his head. No. He had a mission. He couldn’t afford to think like this. What was done was done. Besides, even Dean and Cas weren’t one hundred percent sold on killing Angela. It wasn’t like she was going to go on a murder spree within the three hours. At least, Angela leaving town meant that she would leave Derek alone and that was a good thing. At least that’s what he told himself. 

“So, what are you guys talking about?” Jack asked happily once he got back to their table. A part of him had hope that they would proudly announce their love for each other and then would drive home as a happy family. Unfortunately, nothing was ever that easy. 

“We were talking about how I would rather be in Minnesota with Sam and how raising your confidence level isn’t a good enough reason to go on a hunt,” Dean snapped. 

Castiel sent Dean a dirty look. “What Dean meant to say was that you’ve been acting strange lately and we think you’re hiding something from us,” the moment the words left Castiel’s mouth his face looked regretful, “I-I didn’t mean to say that.” 

There was nothing Jack could do to prevent the look of hurt from flashing on his face. 

“Me either,” Dean said, looking panicked. 

“It’s fine,” Jack said, stiffly sitting down. He knew that it wasn’t their fault, so he tried to brush it off the best he could. Afterall, he did give them the truth spell, they had no choice but to be brutally honest. “Are you guys okay?” he pretended to be oblivious. 

“Dammit! I think the witch spiked our drinks!” Dean cursed. “Quick! Cas, last week when you watched that old western movie and you told me you liked it, were you lying?” 

“Yes. I hated it,” Cas answered immediately. “It was very boring and predictable. I only said I liked it because it made you happy and I like it when you’re happy.”

Jack couldn’t help himself from grinning at the pink that was spreading across Dean’s cheeks and ears. 

“Um… you, ask me something,” Dean demanded, pointing at Jack, still trying to regain his composure.

“Who’s your favorite Scooby Doo character?” Jack asked, the first question that came to mind. 

“It’s Fred. I only said it was Daphne because that’s what people expected me to say. I can’t help it. That goddamn lovable dumbass,” Dean blurted out, looking slightly pained. This time Jack couldn’t stop himself from giggling uncontrollably. 

“It’s a truth spell,” Castiel said, looking mildly horrified. 

“You,” Dean pointed his finger at Jack accusingly, causing the nephilim to immediately stop laughing. “I saw you take a sip from your drink. It’s your turn to answer a question.” 

Jack nodded nervously, knowing that he wasn’t under the spell. 

“Remember that one time I caught you at three a.m. in the hallway with your sheets in a ball and you were acting weird? Tell the truth, did you have a little accident?” Dean asked, with a wicked smirk.

“No!” he answered a little too quickly as he felt his face heat up.

“Liar!” Dean said accusingly. 

“Alright, so she only poisoned Dean and I. Why?” Castiel said carefully.

“I probably threw her off by getting a different drink,” Jack suggested with a shrug. “And she probably didn’t see me as much of a threat.” He really hoped that answer was sufficient, he didn’t think his plan this far through.

“But why a truth spell? If she knew we were hunters, why not just kill us?” the angel asked thoughtfully. 

“Isn’t it obvious? If you can’t lie, then you can’t work the case,” Jack explained. 

“Dammit! He’s right,” Dean groaned. “If I even try talking to the police the first thing out of my mouth might be ‘hi my name is Dean Winchester and this badge is fake.’ I didn’t even think of that.” 

“So, what do we do?” Jack asked. 

“We get the fuck out of here. Before I accidentally tell the whole room I’m on FBI’s most wanted for murder, robbery, and grave desecration.” Dean quickly covered his mouth with his hand once he realized what he said. Then he dashed out of the coffee shop while angrily proclaiming what sounded like “I hate witches,” muffled by the palm of his head. 

Jack lingered behind and grinned after them mischievously, while pulling out his phone to text Claire.


	10. Chapter 10

**Notes for the Chapter:**

> Happy Thanksgiving! I hope everyone is having a nice day! We are about to enter the drama portion of our story... Just a heads up, I wrote the bulk of this chapter after watching 15 x 18, so I was feeling a little angsty lol.
> 
> Hope you enjoy!

The ride back to the motel room was filled with dead silence. Clearly, Dean and Cas were both too afraid to open their mouths. Jack couldn’t allow that. If this was going to work he needed them to talk. 

“So, if we can’t work the case. What are we going to do?” he asked innocently, leaning forward from the back row so that his head was between the two.

“Call Rowena. Break the spell. Kill the witches,” Dean gritted out, purposely keeping his sentences short. 

“And if she can’t break it?” he asked, already knowing what the witch’s response would be. 

“Then we learn sign language,” Dean grunted.

“This is powerful magic, I’m sure it can transfer across other languages,” Cas pointed out.

“It can’t be that bad,” Jack wondered out loud. “In my experience, lying always leads to problems. Maybe it’s a good thing.”

“Yeah? Easy for you to say Mr. I’m-too-innocent-and-adorable-for-monsters-to-target-me,” Dean mocked. He was obviously unhappy that Jack got away without being bewitched. 

“You’re just jealous,” Cas said pointedly. 

“Of course I’m freakin’ jealous Cas! We literally can not lie! Do you even know how much of my day is spent lying? It’s my freakin job!” Dean snapped. “Innocent kid my ass,” he added with a growl.

“It’s all a part of my charm,” Jack said with a grin, to which Dean rolled his eyes. “I think this might be fun! We can learn more about each other!” the nephilim said excitedly. 

“Jack, we’ve raised you from birth. I’m certain there is very little we don’t know about you,” Cas said with a sigh. 

“Yeah, I think we know too much about each other,” Dean scoffed. 

“You guys know a lot about me, but I don’t know that much about you. You’ve known each other for nine years longer than I have and you’ve barely told me anything that happened,” Jack said honestly. He really did want to know more about their past. They would only tell them a bullet point version. Cas raised Dean from hell, the Winchester’s started and stopped the apocalypse twice, God came back then left again, then Jack was born. He had a gut feeling that there was a lot they were leaving out. 

“That’s because it was a shitty time and we did a lot shitty things,” Dean bluntly. He was clearly not in the mood to answer the three year old’s questions. “Also, it’s because we’re trying to protect you from the truth because if you knew what we’ve done you might look at us differently.” Apparently, he didn’t mean to say the last part going by the way he hit the steering wheel in frustration immediately after. 

“I wouldn’t look at you differently. I’ve done bad things too,” Jack added, hoping that they would find it reassuring. 

“At least everything you’ve done was by accident,” Dean mumbled. 

“Jack, you don’t want to know our past. Maybe one day we’ll tell you the good parts, but the bad parts I’d prefer it if I never told you at all,” the angel sucked in a breath. It seemed like the truth spell betrayed him as well. 

“At least you told me the truth,” Jack attempted to joke, but it fell flat. “Maybe you can tell me about something else. Like…” he thought about it for a moment, “Tell me more about your dad Dean!” 

“Oh look we’re here,” Dean said abruptly pulling the car into park and practically flying out the door. 

“Sore spot,” Cas told him with a grimace before following. 

Jack hopped out of the car with a sigh. He could tell that this was going to be difficult.

“Kid, you do realize that it’s a truth spell not an answer-to-anything-you-ask spell,” Dean told him as he unlocked their motel room. 

By the time all three had entered the room, Dean was already calling Rowena on speaker, just as they anticipated.

“That bitch Angela cast a truth spell on us, so we need you to get your ass down here and fix it!” Dean barked angrily into the phone. 

“That’s hilarious darling, but you know I don’t answer to that tone,” she said in an amused drawl. 

“Fine. Rowena, would you please help us?” the hunter rolled his eyes. 

“That wasn’t very convincing, but _fine_ ,” she sighed dramatically. “Now, tell me what happened from the beginning.” 

Dean recounted their story from the beginning of the case to the coffee shop in a clipped tone. “Now, Cas and I can’t lie, which is a big freakin’ problem when you’re us!” 

“Let me get this straight, you and Castiel were enchanted, but not Jack.” The nephilim held his breath, why was she bringing attention to his lie if she already knew the truth? If Dean and Cas ever figured it out it was him, not only would it ruin the plan, but they would be really mad with him. 

“Yeah, can you explain that to me? Why would she let him off?” Dean asked, scratching his head. 

“I don’t know how her mind works,” Rowena says with a sigh. “It could be for a number of reasons. Maybe it was the drink mix up. Maybe she used all the potion she had on the first two. Maybe he said something nice to her at the register and she felt guilty. Or maybe she just saw him as less of a threat. I don’t know.” 

“Seriously? That’s all you got? Come on Rowena we need an MO,” Dean angrily rubbed a hand down his face. “Fine. So what, are you saying she’s got a thing against hexing kids?” 

“I doubt she has any type of standard,” the witch snapped. “Of course that’s not the reason. Jack looks like an adult, only those that know him know his true age. As for your MO, you’re hunters who have been investigating the death of someone she murdered. What more reason does she need?” Rowena spoke slowly as if she believed it would be difficult for them to understand otherwise. 

“But why a truth spell? Wouldn’t it have been easier for her to kill us?” Cas spoke up, moving closer to where Dean was holding the phone. 

“Not all witches are bloodthirsty Castiel,” Rowena tisked. “A truth spell is far less messy and even the police could trace poison back to her. Also, every witch knows that all hunters are liars. Without being able to lie you will barely be able to walk outside let alone finish the investigation. Besides, by the time it wears off, Angela will be far away from here.” 

“But, we don’t have to worry about that right? Because you're going to get down here and fix it. Right Rowena?” Dean sounded slightly panicked. 

“Ooh, I’m sorry lads I wish I could, but I’m in Reno right now. It would take me over a day to reach you. By then I’ll just be wasting my time,” she said in a fake sympathetic voice. “I would tell you the countercurse but I’m afraid the ingredients aren’t easily accessible. Even if you did manage to get them the level of expertise the spell would require, I’m afraid none of you possess. If Samuel were there I’d feel comfortable passing the information to him knowing he’d stand a chance, but unfortunately he’s not.”

“Dammit!” Dean cursed. Jack was surprised by his reaction to the spell. Of course he expected him to be upset, but he thought it would be more of an annoying inconvenience instead of genuine anger. Even that didn’t compare to Castiel’s reaction. Jack had never seen his father figure look so horror stricken, unless somebody’s life was at stake. The sight struck a fearful chord deep within the young nephilim’s gut. 

“Please tell me we’re not stuck like this,” Cas asked, sounding desperate. 

“Don’t worry,” her voice softened. “As long as you’re not foaming at the mouth or unwillingly spilling all of your darkest secrets, then I am sure it’s only a minor spell. Angela is not exactly an advanced witch, it should wear off in three hours,” she promised. Dean and Cas seemed to relax slightly, but they still looked tense. 

“Okay great. Thanks Rowena for nothing,” Dean gave a snarky remark before hanging up. “Dammit! I knew we shouldn’t have gone on this case! I had a gut feeling about it and I ignored it.” 

“If you didn’t want to come so badly then you shouldn’t have,” Cas growled, crossing his arms. “Just admit it, you wish you went to Minnesota with Sam.” 

“Fine Cas! I’ll admit it! I _do_ wish I went with Sam!” Dean lash out. He turned his back on them trying to calm down.

“If you didn’t want to come then why did you?” Castiel asked quietly. Dean didn’t respond, firmly keeping his back towards them, so Cas continued. “It’s been obvious from the beginning that you only came on this hunt to spare Jack from feeling rejected. Going off on your own, leaving us at the police station, you didn’t want to work this case with us. You would rather work it by yourself.” 

Dean winced. “Cas that’s not —“ 

“Yes it is,” Cas insisted. “I get it. You would rather spend time with your brother instead of us.”

“Dammit Cas!” Dean finally turned around. “Spending time with you and the kid is the only reason I did come!” 

Jack was sitting on the edge of his seat. He didn’t dare to say a word. Claire told him to just let them talk it out and that’s what he planned to do. 

Cas scoffed. “I find that hard to believe.”

“Fuckin’ truth spell Cas. Couldn’t lie if I wanted to,” Dean bitterly mumbled. 

“Well, you have a terrible way of showing you care,” Cas said bluntly. 

Dean rolled his eyes. “Look, the reason I went off on my own was because I was trying to keep you safe.”

This time Cas rolled his eyes. “Since when have any of us cared about safety and last time I checked you’re the only human in this room. Your fragile bodies are much easier to maim.” 

“I didn’t mean it like that,” Dean corrected, choosing to ignore Cas’ insult. “I just meant that witches are tricky. And sometimes you and Jack can be a little... “ He trailed off trying to come up with a word that wouldn’t be insulting.

“What?” the angel narrowed his eyes.

“You’re too trusting,” Dean admitted with a wince. He looked like he wanted to try and fix it, but what came out of his mouth instead was, “You have a history of believing people’s bullshit.” 

Cas’s eyes darkened. “So you’re comparing my judgement to that of a three year old.” 

“Hey!” Jack protested, recognizing the insult for what it was. He was getting tired of people assuming that he was naive because of his age. He knew that there was a lot about the world he didn’t know, but that didn’t mean he knew nothing. He wasn’t a child that knew nothing outside of sunshine and rainbows.

“Jack, I didn’t mean it like that,” Castiel’s face quickly changed from angry to guilt as he turned from Dean to Jack. “I shouldn’t have said that as if being compared to you is insulting. You are very advanced for someone your age.” The nephilim wrinkled his nose trying to work out whether that was really a compliment. On one hand he called him advanced for someone his age, but most people his age were still being potty trained. 

“You know what Cas,” Dean said, ignoring Jack’s sidetrack. “This is freakin’ ridiculous. I’m not going to spill out all my dumbass feelings just cause a witch made me. I say we sit here quietly and wait out the three hours.” 

“Agreed,” Castiel answered before Jack could even get a chance to argue. 

“Awesome,” Dean let out a breath of relief. “I’m going to take a nap. No one bother me,” Dean warned. The Winchester proceeded to plop down on the bed, lazily kick off his shoes, then rolled on his side facing the wall. 

Jack was aware that this put a huge dent in their plan, but he didn’t dare stop Dean. His warning had a hint of finality to it. Jack was well familiar with Dean’s “we’re doing my idea or else” tone of voice and he knew that trying to fight it would end in disaster. 

“Here. You can watch the television,” Cas handed him the remote. “Try to keep the volume low,” he added, after sparing a glance towards Dean.

Jack obediently took the remote and moved to sit at the end of the bed not occupied by Dean. He flipped the channel to the first cartoon he found that wasn’t for babies or adults. He decided to accept defeat for now. He was on a time crunch, but he figured he could afford wasting an hour while he thought of a new way for them to talk. 

“What are you going to do?” He asked Cas who was solemnly looking down at his lap. 

“I was going to sit here quietly,” Castiel shrugged. He further explained after noticing Jack’s puzzled look, “Sitting quietly is actually a common activity among angels. They call it seeking revelation, it’s a meditation of sorts. Some angels do it to listen to angel radio, others will sit for hours hoping that God would speak to them. Of course I do neither of those things. I do it because it gives me time to think.”

“What do you think about?” Jack asked curiously. 

“Everything,” Cas answered with gleam in his eye. “The universe, earth, heaven, hell, humans, angels, demons. I think about my life and the people in it. Those I care about, those I don’t. Dean, Sam, you.” He ended with a small smile gracing his lips. 

“That sounds nice,” Jack said softly with a smile of his own.

“It isn’t always,” his face suddenly turned somber. The angel plastered on a smile, “Don’t worry about me. Go back to your cartoon about the biologically inaccurate sea sponge.” 

That didn’t stop Jack from feeling concerned, but he nodded and did as he was told. However, his mind wasn’t fully focused on the screen. He was busy wracking his brain for ways to get his surrogate parents to start talking. This was a delicate situation that required subtlety, which unfortunately was not the nephilim’s strong suit. The second episode was starting and he was starting to feel frustrated as he still had no ideas. He considered texting Claire, but he was afraid that she wouldn’t answer in time. 

Dean suddenly woke up with a gasp that quickly turned into a groan. The movement was so abrupt Jack was startled out of his thoughts. 

“How much longer?” Dean mumbled half awake. 

Jack looked down at his phone, “It’s been an hour and forty five minutes since we left the coffee shop. So at least another hour left.” 

Dean groaned loudly then collapsed back on the bed throwing a pillow over his head. Jack decided that he needed to act soon and fast. He only had an hour left and he couldn’t let Dean sleep through it. He also couldn’t wake him up without risk of being attacked. He concluded that his best chance was to start with Castiel. He would be more willing to open up to him anyway. 

He waited until Dean’s breathing evened out to talk. “What do you think he’s dreaming about?” he asked Cas. 

“I'm not sure Jack,” Castiel sighed. The boy kept quiet hoping that he would keep going. “A long time ago I used to know: sometimes I would dreamwalk into his mind. Most of the time it was to relay a message whenever I couldn’t reach him, but a few times I did it out of curiosity. His bad dreams were usually about his experience in hell or losing people he cares about. I didn’t like those dreams. If I saw that I would usually wake him up, not entirely, but at least enough to knock him out of REM state.

“I also saw his good dreams, those were my favorite. Sometimes they would be old memories or average days in his life, but most of the time they were peaceful. I was surprised that someone with such a rambunctious personality would have such soothing dreams. Sometimes they would feature him fishing on an old dock, other times he would be driving down a never ending stretch of road. But no matter what he was doing there would always be an orange sunset in the background. It was… beautiful.” He ended with a found smile. 

“Why did you stop?” Jack asked. 

“He asked me too,” he said with a hint of sadness. “He said it was an invasion of his privacy. I didn’t understand what he meant at the time, but now that I’ve experienced dreaming myself, I get it. I know that dreams are uncontrollable, unpredictable, they can expose the deepest parts of your inner psyche. They’re personal and not meant to be seen by others.”

“Do you ever wish you could?” 

“Sometimes…” he said with a faraway look in his eye. “Not because I wish to invade his most private thoughts. I just sometimes wish I could be on that dock by the lake again… with him. It’s the only time I’ve seen him without stress, without worry, without anger, just truly at peace. For me, being able to see him so content, it made me feel happy.” 

In a soft voice Jack dared to say, “You care about him.” It wasn’t a question. It was a statement, an observance that was near impossible to ignore. 

“Of course I do,” Castiel said plainly, staring at him slightly puzzled. 

“I know. That’s not what I meant,” Jack pushed. “I don’t mean that you like him. I mean you really _care_ about him,” he emphasized hoping the angel would understand.

“I do,” Castiel answered after thinking about it for a moment. “Dean is the person I love most in the entire world, with only you holding a contest. Even then I couldn’t compare the two. The love I feel for both of you is strong, but entirely different. It’s not a bad thing, it’s just… different. In fact, I don’t think ever felt for anyone in the way I feel for Dean. I owe everything I have to him, including the love I feel.”

Jack was completely entranced by every word Castiel was saying. It made him feel a wonderful warmth growing from inside his chest. Although that didn’t prevent him from noticing the way Castiel’s eyes seemed glazed over as he spoke and he immediately knew that the angel wouldn’t be this open about his feelings if it weren’t for the spell. The angel seemed to be speaking from a faraway haze as his eyes were looking directly down at the table in front of where he was sitting. Which is why neither of them were prepared for the voice that rang out from behind them. 

“Cas, what are you saying?”

Both the angel and the nephilim whipped around to look at Dean who was now sitting straight up with no trace of sleep left on his face. 

“D-Dean,” Cas stuttered, sounding mildly horrified. “I thought you were sleeping.”

“Yeah, well it turns out I wasn’t,” Dean was now standing up walking towards them. “Now what were you saying?”

“I didn’t mean for you to hear that. I was just talking to Jack,” Castiel tried to explain weakly.

“Except I did hear it. Stop avoiding the question Cas.” Dean’s face was blank. Entirely unreadable. It made Jack feel a little uneasy. 

“I didn’t mean to say any of that. It was entirely the work of the spell.” The angel tried to cover up once more. 

“Cause you kinda sounded like you were trying to say… B-but you couldn’t possibly mean that…” Dean sounded like he was about to freak out and Jack couldn’t understand why. Castiel’s words had made him feel all warm and excited, but Dean’s face looked like he was feeling anything but that.

“Exactly. What I was trying to say was... “ Castiel took a deep breath like he was trying to concentrate on what the next words out of his mouth would be. “What I was trying to say was that I love you.” Clearly that also wasn’t what he had planned to say because Cas’ eyes became as wide as saucers. 

Meanwhile Jack was feeling thrilled. This was it. This was what all of his and Claire’s planning had finally amounted to. Dean and Cas were going to admit their feelings for each other, then they would all go home together, and it would be a happy ending. Jack was already thinking about what he would say to Claire when he called to tell her their plan was successful. He was ready for their new lives to begin.

That was until he saw Dean’s face and he realized that the elder Winchester looked equally as terrified as Cas. He even swore he saw a hint of anger. 

“Jack, wait in the car,” Dean suddenly demanded.

“What?” He blurted out, shocked. That was definitely not what he was expecting him to say. 

“You heard me. Go wait in the car. You shouldn’t hear this.” Dean repeated, this time with more bite. 

“B-but,” Jack stammered still in shock. He didn’t want to wait outside. They were reaching the climax of their conversation and he didn’t want to miss it. 

“Jack. Go. Now. Wait in the car, go get some food, follow a fucking bee. I don’t give a fuck about what you do as long as it’s not in this room.” Dean’s voice had an edge to it that Jack knew better than to disobey. So, with one last nervous glance towards Castiel he stood up and walked outside. 

He acted like he was following Dean’s orders up until he was on the other side of the door, because there was no way he was missing this conversation. The second he closed the door he pressed his ear up against it hoping that his powers gave him the advantage of enhanced hearing. He closed his eyes and held his breath trying to concentrate solely on listening. After a moment of silence he was about to give up when he finally heard Dean’s voice. 

“Don’t do this Cas,” Dean pleaded. “It’s the spell that’s making you say it, this isn’t you.There’s no way you…” 

“You’re right,” Castiel said so quietly that Jack had to strain to hear it. “The only reason I’m saying this is because the spell made me.” Jack swore he heard Dean sigh in relief. “But I can’t take it back. I-I won’t take it back. Because if I did I’d be lying to you. I would be lying to myself. And we both know I can’t do that.” 

“Cas, no…” he heard Dean say weakly. 

“I’m sorry. I didn’t mean for you to find out. Especially not like this,” Castiel apologized.

“Dammit!” Dean suddenly cursed followed by a thud. He imagined that Dean probably knocked something over. “Don’t be sorry Cas. You have nothing to be sorry for. I’m just trying to figure out how someone like you, could be in love with a sorry piece of shit like me. Seriously. What is it about me that’s such a catch? I’m angry half the time because it’s the only way I know how to express emotion. I’m a total asshole. I’m an asshole to you, I'm an asshole to your son. You know that I hated him the first month of his life? I mean it I truly _hated_ him. Don’t even get me started on the amount of daddy issues -“

“Dean, stop it!” Castiel interrupted Dean’s rant angrily. “You don’t get it! You see yourself in such a negative light I don’t think you ever could understand. I don’t see you as some angry, heartless machine and trust me, I am saying that as someone who used to be one. I see someone who feels love so strongly, so passionately that it’s unbearable for him at times. It drives everything you do. _That’s_ what I love about you. 

“I know you and Jack may not have gotten along at first, but you do now. I see the way he looks up to you. The way he’s always trying to follow your footsteps. You’re his hero. And I know that you care about him in return. I see it on your face and it only makes me love you more.” 

“Cas stop,” this time Dean interrupted. “You deserve better than me, you’re just too insecure to see it. Even if that weren’t true, this can’t happen.” Dean spoke quietly, his voice laced with guilt. 

There was a long silence that rang out, neither of them daring to speak. Jack was feeling nervous, this conversation was not going how he expected it to. 

“I know you don’t feel the same way,” Castiel finally said. “So, I’m going to make this really easy for you. I promise we can just forget that this conversation ever happened. We can just decide that this was a mistake caused by the witch. We can go home and continue on like we’ve always done. I just need you to do one little thing for me.” 

“What?” Dean asked, sounding a little frightened. 

“I need you to say it out loud. Tell me this is not what you want. Please. Then I can finally move on.” Castiel sounded like he was practically begging. The sound alone made the nephilim feel slightly ill. 

There was another long silence that followed. Every second that past made Jack’s anxiety double as he dreaded Dean’s response. 

“Castiel,” Dean started, his voice no longer sounding scared or weak. This time it sounded strong, confident, but also cold, unfeeling, numb. “There can never be anything between us.” 

Jack felt as if an ice cold bucket water had just been dumped on his head. 

“You got that? Nothing. With our lives, we can’t even afford to consider the possibility. So please, for both our sake’s, take your feelings and shove them back down. I’ll forget about it and so will you because that’s never going to happen. Ever.” 

Jack felt like all of the air had sucked out of his lungs. He felt frozen in shock. His mind was reeling. He had no idea what to think, what to do, how to feel, how to breath. The only thing that snapped him out of his spiral was the long shriek that rang out from his phone. It took every bit of restraint he had in him to calmly press the stop button instead of smiting his phone into a pile of dust. 

That was the wake up call he needed to grasp the reality of the situation. This was his fault. All of it. He was the one to spike their drinks, he was the one who made Cas open up, it was all him. He was the one who got his father into this mess and needed to be the one to get him out. He needed to make this right the only way he knew how. 

Jack flung the door wide open. Both Dean and Cas turned towards him, practically jumping out of their skins. Dean looked like he was seconds from forcibly making Jack leave, so he held up his phone as if it was a white flag. “Um… it’s been three hours,” he told them with a gulp. 

Dean visibly relaxed, “Thank god. Okay we’re leaving. Now.” The Winchester stuffed a few things into his duffle bag then pushed past Jack and made his way to the car. 

The ride home was unpleasant to say the least. The first hour was filled with complete silence. Jack didn’t dare say a word, while Dean and Cas clearly weren’t in the mood for talking. Eventually Dean turned on his music, keeping it at a low volume which helped with the awkwardness. This type of uncomfortable silent ride was usually reserved for one thing: failing a hunt. In a way it was true, but they all knew it was so much more than that. 

It didn’t feel right. Dean’s music was playing, but the hunter’s bad singing wasn’t going along with it. The car was absent of Dean and Cas’ usual bickering about nothing serious. Even Jack didn’t feel like asking his usual stream of random questions. Dean never stopped once, not for food, or gas, or to use the restroom. He was determined to drive straight home. 

Between the long drive and the lack of conversation, Jack really had time to sit with his thoughts. What started off as feeling sadness and guilt slowly morphed into anger. He couldn’t even pinpoint who he was angry with, it was like his rage was pointed in every direction.

He was mad at Claire for talking him into her “getting Dean and Cas together” scheme in the first place. He was mad at Rowena for giving them the idea to use the truth spell. He was mad at Angela Dealy for killing Cassidy Jackson just so she could date her fiance, then for having the nerve to thank him for the distraction. He was mad at Sam for texting Claire that “Dean and Cas were definitely in love” and for declaring he knew his brother better than anyone when clearly that wasn’t true. He was mad at Dean for rejecting Castiel, despite the angel being the most selfless and loving person Jack had ever met. He was mad at Castiel for thinking so lowly of himself that he fell in love with someone he knew would never love him back. But most of all, Jack was mad at himself. For lying to and causing pain to two people he cared about.

It was a relief the moment the Bunker’s rusty front entrance came into view. The moment the gear shift was switched to park, Castiel fled the car and retreated into the Bunker. Jack had been expecting Dean to do the same thing, but instead the hunter lingered in the car for a second. 

“Look, Jack I’m sorry about kicking you out of the room earlier,” Dean spoke up to the three year old’s surprise. “I looked back on it and realized that was probably a dick move from your perspective.”

“It’s fine,” Jack shrugged. “I understand why you did it.” It was a private moment between the best friends and they didn’t want him intruding. He never really thought about it too hard until Dean brought it up. 

“Yeah, but you don’t know all of it,” Dean mumbled. “Look,” he continued only louder, “when I was a kid, around four years old, my parents used to fight all of the time. They didn’t give a damn about if I was there or not. They probably assumed I was too young to understand it, but I wasn’t. I knew they were fighting; and that memory has stayed with me since. It’s one of the few memories I have of my parents being together and I hate it. I hate that it’s what I think of, but it is. Looking back on it I can’t help but think that maybe if I wasn’t there, I would have a better memory in its place.

“Anyways, my point is that shit stays with you. Besides, you already have enough crap to work through, you don’t need to pile our dumbass fight on top of it. I just didn’t want you thinking that it was because of something you did. Capiche?” 

Normally, Jack would have found the sentiment kind of sweet. The idea that Dean cared enough about his well being to not make him witness something potentially upsetting. It would be kind, if it weren’t irrelevant from the truth. Because Jack wished he listened to Dean’s advice. He wished that he didn’t listen. Blissful ignorance was looking far better than the heart wrenching reality. Sure he would have been confused, but at least he wouldn’t have this black hole of anger and guilt eating him from the inside.

Which is why, instead of giving Dean a proper answer, he gave him a small smile and nod of understanding before hurrying inside the Bunker. He headed straight to his room and closed the door. Jack paced back and forth, trying to get his feelings in order. He needed to let out this slowly building mass of emotions in a safe matter and that usually meant curling into a ball and crying. But the angry part of him didn’t want to cry. He already felt enough shame today and crying would only make it worse. He only stopped pacing once he noticed the light bulb above his head was beginning to rapidly flicker. He took a deep breath, the last thing he wanted was to lose control. He didn’t think he could accidentally hurt someone from inside his room, but an exploding light bulb would be hard to explain. 

Once he had his breathing under control, Jack pulled out his cellphone. Without giving it much thought, he tapped on Claire’s name and before he knew it his room was filled with the sound of ringing. 

“Jack!” Claire answered excited. “Did it work? Tell me everything!”

“It didn’t work,” Jack croaked out. He couldn’t tell if his voice sounded that way from emotion or lack of use. 

“What do you mean it didn’t work? Was there something wrong with the spell? Did that witch screw you over?” she suddenly sounded on guard.

“I mean, we were wrong Claire. You were wrong!” Jack said accusingly. “They don’t love each other and they never will. All we managed to do was screw everything up.”

“Are you sure? Maybe you heard it wrong? Tell me exactly what happened.”

“I got Cas to admit that he loves Dean, but Dean doesn’t love him back. He turned him down and now they won’t talk to each other,” he summarized, not really in the mood to retell everything. “This is all my fault,” Jack’s voice cracked. 

“This isn’t your fault, Jack.” Claire spoke softly, it sounded uncharacteristic for the rugged hunter. “Dean will come around eventually, he’s just stubborn. Maybe if we try something else -” 

“No!” Jack insisted. “I’m done. Dean was under a truth spell, which means he wasn’t lying. He’ll never come around. So I am done with the plans, the lying, all of it.” 

“Jack, wait-” 

“I told you that lying always ends badly, but you wouldn’t listen,” the nephilim whispered, his vision blurring. 

“I’m sorry,” Claire sounded guilty. 

“Don’t call me again.”

Jack ended the call before she could say anything else. Then he sat on the floor, hugged his knees to his chest, and finally allowed himself to cry.

**Notes for the Chapter:**

> I hope this chapter didn't feel too much like one sided Destiel. Just letting you know that's not where this is going. This story will have a happy ending! Dean just likes to make things difficult lmao.


	11. Chapter 11

**Notes for the Chapter:**

> Hello everyone! I hope you've been having a good 2021! So, this chapter and the next chapter were originally supposed to be one chapter, but it was getting to be too long so I decided to split it up. So hopefully the next chapter should be up soon since it is almost finished. 
> 
> Also, I know I've been really behind with responding to comments. So, I plan on working on responding to all of them today. Thank you!

Claire really screwed up this time. 

The worst part was she couldn’t even pinpoint exactly where she went wrong. All she knew was that Jack hated her and there was this lump of guilt that had settled deep in her gut. 

The nephilim really wasn’t kidding when he warned her to never call him again. She waited a day before she tried calling, hoping that he’d cool down enough to think straight, but she wasn’t successful. She tried everyday for a week, but every time it went straight to voicemail. She sent text after text apologizing and she’s heard nothing back. 

She tried really hard to not let it bother her. After all, she hadn’t known Jack for very long and it wasn’t like he was someone that she saw often. In the big picture, the loss of his friendship shouldn’t bother her at all, but then why couldn't she get their last conversation out of her head? 

The worst part was, she couldn’t figure out what she did wrong. She replayed that last phone call with Jack over and over in her mind and everytime she concluded that she was innocent. 

Claire still firmly believed Dean and Cas were in love with each other. Dean was just too stubborn to admit it. She could hardly be blamed for his unwillingness to express emotions. Also, it was the witch’s idea to use the truth spell and it was Jack who trusted her. Claire told him it was a bad idea, but he wanted to go through with it. The witch probably wanted them to turn against each other. So really, none of it was her fault. 

Except, if that was true, then why did she feel so bad?

She gave up on calling him after the last time her phone gave her an electric shock before going to voicemail. It didn’t really hurt, but it was enough to make her throw her phone in surprise. She had a feeling that it wasn’t a coincidence. 

After that incident she tried just accepting that she would never get a hold of him and move on. Except Claire was a girl of action, which meant that doing nothing only made her guilty lump feel worse. She had hoped that going on a hunt and killing something would be enough to make it go away. But by the time the hunt was over and she was wiping the vampire blood from her machete, she found that the feeling was still there.

Disappointed and feeling like crap, she drove back to Jody’s wondering if there was anything she could do to make her feel better. Once she got home she immediately plopped down on the couch next to where Alex was watching TV. 

“Rough day?” Alex asked with a smirk.

“More like rough week,” Claire sighed, turning sideways so that she was lying on her back with her feet dangling off the side. She covered her hands with her face and let out a groan. That’s when she heard the now irritating sound of Lindsay Lohan’s fake British accent come out of the television. 

“Can you change it to literally anything else?” she whined. This was the last thing she needed to be watching. It was the movie that got her into this mess. 

“I just finished working a ten hour shift at the hospital. I get to watch whatever I want,” Alex said, clearly not caring about her feelings. 

“Seriously Alex, I do not want to watch this movie,” she snapped. 

“And I told you that I worked a long shift. Something you wouldn’t understand.” 

“What do you mean? I just came from a job.” Claire scoffed. 

“Yeah and how much did you make?” the brunette teased. 

“Low blow,” Claire frowned. She hated whenever Alex gave her slack about being a hunter. Just because she had a “real job” doesn’t make it any less important. When it came down to it, they both saved lives. 

“Does your sudden hatred of the Parent Trap have anything to do with your dumbass plan with Jack?” Alex looked at her knowingly. 

“Maybe,” Claire mumbled, not enjoying how easily Alex could see through her. 

“Is he still not talking to you,” Alex’s face softened. 

“No. Pretty sure he hates me,” Claire said moodily. 

“Well, it was a dumbass plan.” 

Claire sat up suddenly to throw Alex a glare. “You can’t say it was a bad idea when you helped us come up with it!”

“Yeah in the beginning, when all we did was prank call Cas to make Dean jealous. Then the two of you went off on your own and I forgot about it.” Claire rolled her eyes, she just knew Alex was going to find a way to blame this on her. “If I was in on it, I could have told you that a truth spell was a bad idea. You can’t force people to talk about their feelings. That doesn’t actually solve anything.” 

“This isn’t my fault. It wasn’t even my idea, it was Jack’s. Or it was that witch that _he_ said we could trust.” Claire argued, determined for this conversation to not turn against her. 

“Didn’t you say that Jack is only three years old? Obviously he doesn’t know what he’s doing. You’re the adult, which kind of makes you responsible,” Alex talked as if it were obvious. 

“Great. You’re trying to say this is my fault.” Claire was beginning to feel annoyed. She really regretted not going straight to her room. 

“I’m not saying this is entirely your fault. It’s Jack’s fault too. I’m just saying that you should take some responsibility.” Alex said calmly, trying her best not to piss off the young Novak. 

“Fine,” Claire gritted out. “What do you think I should do?” 

“I don’t know what you should do about Dean and Cas, but I think they need to work things out for themselves. You should try talking to Jack,” Alex told her with a sigh. Claire didn’t respond. She didn’t see the point in pointing out the obvious fact that Jack didn’t want to talk to her. “Hey, you said this movie was what got you into this mess, maybe it’ll give you an idea about how to get out,” Alex joked while turning up the volume with the remote.

A part of Claire wanted to ignore what Alex was saying and storm off to her room right now. However, the superior part was too tired and depressed to move and figured she didn’t have anything else to lose by watching it. Maybe somehow it would give her an idea. 

She watched the movie for a while with little interest. Her attention wavering in and out, until one scene in particular caught her attention. 

She sat up straight. “That’s it. I know what I have to do!” 

“What?” Alex asked, looking at her strangely. 

“We can’t force Dean and Cas to talk to each other, they have to realize it on their own,” Claire explained, already forming a plan in her head. 

“That’s literally what I’ve been telling you,” Alex sounded unamused. 

“Yeah, but… “ Claire trailed off unsure how to explain it. “I thought of an idea of how we could make them do it.” 

“How?” Alex asked, staring at her like she was crazy, but Claire didn’t care, her mind was already far away. 

“Parent Trap,” Claire grinned. Alex still looked confused, but she didn’t have time to explain it to her. She stood up and ran off to her room, vaguely hearing Alex yelled out, “Your welcome!” 

The first thing she needed to do was get Jack on board with her plan. She couldn’t do it without him, or at least, she didn’t want to do it without him. It was a weird feeling once she realized just how true it was. For years, she was content with doing everything by herself, but going it alone was just that, lonely. Claire was beginning to realize that she had enjoyed the boy’s company more than she would like to admit. Dean had warned her that Jack had a way of growing on people and that was exactly what happened. Just the idea that the doe-eyed boy now hated her, didn’t sit right with Claire.

Her only problem was that Jack didn’t want to talk to her. Calling or texting him was out of question, she’d been trying that for the past week. It was clear that Jack was never going to answer, if he hadn’t already blocked her number. Which means she needed to contact him some other way. The answer was so obvious she wanted to slap herself in the face for not thinking it sooner. Because Claire Novak was a girl of action and she would be damned if she was going to sit around waiting for a boy to call her. 

She quickly shoved her stuff back into her backpack and headed out the door. She needed to leave now if she was going to make it to Lebanon, Kansas before it was too late. 

Once she was in her car, driving down the highway with her music playing loudly, she realized that she already felt a lot better. When she was about twenty minutes away from the bunker she stopped for dinner at a drive thru. As she was sitting back shoving french fries in her mouth, she decided to call Sam. 

“Hey Samsquatch,” she smirked, when she heard the younger Winchester pick up. 

“Claire? What’s up?” Sam said, sounding surprised. She didn’t blame him, it wasn’t often she called and when she did, Sam usually wasn’t her Winchester of choice. Not that there was anything wrong with Sam, they just weren’t as close. 

“I just finished up a case in Kansas and I was wondering if I could stop by? Maybe stay the night? The owner of the motel I was staying at was kind of a creep. Figured that I might as well stay at the Bunker, it’s easier than driving all the way back to Jody’s,” the lie slipped off her tongue instinctually. 

“Yeah, of course you can,” she could practically hear the smile on his face. “It’s pretty quiet over here tonight. I’ve been having a thrilling time of reorganizing the Men of Letters files. I swear their filing system makes absolutely no sense to me,” the nerd let out an embarrassed chuckle.

“Wow that sounds so exciting,” she said sarcastically. “You said it was quiet, is no one else home?” As much as she enjoyed Sam’s company, her plan was for nothing if Jack wasn’t even there. 

“No. Um, I mean Cas has been gone for a couple of days - angel stuff, I guess - but Dean and Jack are here.” 

“Nice. I’ll be there in twenty minutes.” Claire felt relieved that everything was falling into place for once. 

“Okay that’s fine, but - “ Sam lowered his voice, “I should probably warn you first that Jack has been in kind of a funk lately. Really, everyone except me has been in one.” 

“Why? What happened?” Claire asked, already knowing where this was going. 

“I’m not sure. All I know is that Dean, Cas, and Jack went on a hunt last week and they’ve been weird ever since they came back. It had something to do with a witch and a spell… I don’t know. None of them will talk to me about it. Now, Jack rarely leaves his room, Dean’s been really grouchy, and Cas has just been… gone.” Sam sounded concerned. “I don’t know, hopefully your presence will cheer them up. Maybe you’ll have better luck at getting them to talk. I know you and Jack are friends.” 

“I’ll see what I can do,” Claire promised. What Sam didn’t know was that her and Jack weren’t exactly friends right now. He definitely wasn’t going to be happy to see her. In fact, Claire would be lucky to come out of this with her head. She was well aware of the nephilim’s lack of self restraint when it came to his powers. However, if everything worked in her favor, hopefully Jack would be in less of a funk than he is now. 

Sam was the one to let her into the Bunker just as she expected. She quickly understood what Sam meant by it being quiet, if he hadn’t told her otherwise she would’ve thought that no one else was there. The younger Winchester showed her to an empty bedroom where she could dump her backpack.

“Are you hungry? I could make you something. Sandwich, soup, cereal, anything?” Sam said with a hopeful grin. 

“Thanks, but I’m fine. I ate before I came here,” she told him. 

“Okay, well just let me know. If you change your mind, our kitchen is free. There isn’t much in it, but help yourself,” Sam looked apologetic and unsure about what to do next. “Sorry, you didn’t come on a better night. Everyone’s been keeping to themselves today, so there’s not much excitement. There’s a TV in the “Dean Cave” that you can watch if you get bored. Dean will probably give me an earful for it, but it’s the best TV we have. It has cable and Netflix. You should use Dean’s account, he gets really touchy when people mess with his algorithm. Sometimes I like to go on there and play trashy Rom-coms just to screw with him,” Sam laughed.

“I’ll keep that in mind,” Claire grinned. “Do you think Jack would mind if I pop in to say hi?” 

“Yeah go ahead. Like I said he’s been pretty down lately, he could use some cheering up. Maybe you can get to the bottom of why he’s upset. I tried asking Dean about it and he said he isn’t sure why Jack’s upset.” 

“Did he say anything about what happened?” Claire asked curiously, wondering if he knew any details.

“Apparently Dean and Cas had a fight. They didn’t say what it was about, but Dean swears that it had nothing to do with Jack. He said he wasn’t even in the room, but I don’t know. Dean and Cas aren’t exactly subtle when they fight. It affects all of us, no matter how hard they try and keep it to themselves. I told Dean he has to be more considerate about what he does in front of Jack. The kid sees Dean and Cas as like his parents. I’m willing to bet that seeing them mad at each other made him upset,” Sam pinched the bridge of his nose out of stress. “I’m sorry. I shouldn’t be ranting about all this to you.” 

“It’s fine,” Claire kinda felt bad for the big lug. He clearly had a lot to get off his chest. She had no doubt that it was a build up from being stuck in a house full of people that’ve been mopey and quiet for the past week. Claire must be the first person actually willing to talk to him in a while. “There’s a lot more action here than Jody’s. Probably because you guys spend more time together. Although, I’m starting to see that it’s probably for the best that we don’t.”

Sam chuckled. “Yeah I can see what you mean. Here, we’re all each other has. I mean when it’s good, it’s really great. But when it’s bad - “ 

“It’s really crappy,” she finished for him. 

“Exactly,” Sam smiled sadly. “I’m sure we’ll be fine. Just give it a couple more days. Anyways, I’ll get back to my filing. Jack’s room is two doors down on the left hand side. Good luck.” He gave her an awkward pat and a strained smile before leaving her. 

Claire walked to Jack’s door and took a deep breath outside. Here goes nothing. She gave the door a light knock before cracking open the door a bit. She immediately saw the nephilim laying on his bed with his back facing the door. 

“I’m not hungry Sam,” the boy mumbled without turning around. 

“I’m not Sam,” Claire winced. “I’m way too short and far less nerdy,” she added as an attempt at a joke. 

Jack immediately sat up and turned around. He stared at her with a furrowed brow, “Claire? What are you doing here?” 

“I wanted to talk to you. You’ve been ignoring my calls,” she said nervously. 

“I was ignoring them for a reason,” Jack said, refusing to look her in the eye. She willed herself to step fully into the bedroom, closing the door behind her. He didn’t object, which was a good sign. 

Claire took the moment to look around, since this was the first time she’d seen Jack’s bedroom. It had the same standard layout as every room in the Bunker down to the gray and brick walls. Similar to Claire’s own room, it lacked a personalized touch probably due to lack of possessions. As far as Claire could see, there was only a framed picture of a woman on the bedside table and brown stuffed bear next to it. The biggest difference between Jack and Claire’s rooms was that his looked more used. He had piles of dirty clothes on the floor, empty candy bar wrappers strewn across his desk, and his bed was left umade with the blankets crumpled at the foot. 

“Jack, I’m sorry about what happened,” Claire said honestly, daring to step a little further into the room. “But you can’t just ignore me forever. It’s not my fault that it didn’t work like we hoped. You can’t blame me for Dean being emotionally constipated.” 

“I don’t blame you for that. I blame you for making me do the plan in the first place. I blame you for convincing me that they were in love,” he spoke quietly. Then his voice suddenly turned from sad to angry, “Everyone always tells me that I’m naive or that I’m too trusting and I hate it. I hate whenever people say that. I used to never believe it. But now, I think I finally understand.” 

Claire took note of the way Jack’s fist was clenched in his lap. It looked like he was digging his fingernails into the palm of his hand. She knew she needed to diffuse the situation or else things could get ugly. 

“Jack,” she said gently, “I swear that I have never lied to you. This wasn’t just some joke, I would’ve never taken it this far if I didn’t believe it. Besides, if I was wrong then why did so many people agree with me? Alex, Rowena, even Sam thought that Dean and Cas were into each other. I still think they are.” 

“No they’re not,” Jack mumbled. “You’re wrong. All those people are wrong. They must’ve just seen Cas’ love for Dean and assumed that he felt the same way.” 

“What did Dean say exactly? You were pretty vague in your phone call,” Claire asked, curious. 

“He said that they would never be together,” Jack looked annoyed that she was making him relive that moment. 

“Okay, but did he ever say that he didn’t feel the same? In those exact words,” Claire suddenly asked, hopeful. Maybe Jack was so distraught by Dean’s outburst that he didn’t take a moment to really think about it. If Dean never said he didn’t have feelings for Cas, then the truth spell didn’t fail them. Dean just found a way to turn him down while avoiding the truth. 

“He said that there could never be anything between them and that Cas should just shove down his feelings,” Jack said, grumpily. He clearly had not caught on to Claire’s thinking. 

“Don’t you get it Jack? Just because Dean _thinks_ that they could never be together doesn’t mean that he doesn’t feel the same. He has low self esteem, he probably thinks he doesn’t deserve Cas.” Claire swore she saw a flash of hope in Jack’s eyes. 

“He did say that he didn’t understand why Cas would like someone like him,” Jack had his brow furrowed as if he was thinking it over. 

“See? That means there’s still a chance.” 

Quickly Jack shook his head, “It doesn’t matter. I told you I’m done with lying and going behind their backs. If they’re in love, then they have to work it out themselves.” 

“I agree with you. They do need to figure it out themselves,” she enthusiastically agreed. “Look, I really am sorry about what happened. The truth spell was too far and I should’ve stopped you from going through with it. But I think I have an idea to make it better.” She looked at him hopefully praying that he would give her a chance. 

“Claire,” Jack started with a sigh. She could tell that he was about to repeat himself so she interrupted. 

“I know you’re done with lying and all that,” Claire rolled her eyes. If Jack was planning on being a hunter then he was going to have to get used to lying at some point. “But I have a plan that doesn’t involve lying or going behind anyone’s back.” 

“I don’t know…” Jack said, looking nervous. 

“Come on, at least hear me out. You can say no to me after,” Claire pleaded. “I can’t do this without you. Or at least, I don’t want to.” She was hoping to appeal to Jack’s soft nature. Claire was rarely ever this candid with her feelings and she couldn’t imagine that Jack ever heard it too often considering he lived with the Winchesters. 

“Okay,” Jack said quietly, his face looked like a mix between guilty and scared. “What’s your plan?” 

Claire grinned wide. “Parent Trap,” she repeated what she told Alex. At Jack’s puzzled expression she continued. “I figured that it was the movie that got us into this mess, maybe it can get us out,” she rolled her eyes, “I mean technically, it was Alex’s idea, but I’d prefer to not give her the satisfaction. Here it’s better if I show you.” She pulled out her phone and took a seat next to Jack on his bed. She played the scene where the twins trick their parents into going on a dinner date on a boat. When the scene was over she finally looked at the nephilim who’s eyebrows were still scrunched. 

“I don’t understand,” he finally said. “You want us to recreate the night Dean and Cas met? You do know they met in a barn? Or did they technically meet in hell?” He tilted his head in a way that resembled Castiel so much Claire almost felt irritated. 

“No. You doof. I just meant the dinner date part. I figured we could make them dinner and set up the date here in the Bunker. We can make sure Sam is gone, so that way it’ll be just the two of them. Dean and Cas will be in control of the conversation and what they choose to say, our job is to just set up the environment. It’s full proof. Even if they don’t end up confessing their feelings, it’ll at least force them to talk and then they can finally stop avoiding each other.” 

Jack was quiet for a moment, probably taking in everything that Claire said. Then suddenly his face changed and he broke out into a grin. “I like it.” Claire felt herself release a breath she hadn’t realized she was holding. “And you’re sure there’s no lying?”

  
  


Claire smirked, “Fine, we might have to give a little white lie about why we’re cooking them dinner, or why we aren’t eating with them, but it’s not a big deal! I can do it for you. You just have to shut up and smile.” 

Jack seemed to accept that answer because he frowned and asked his next question. “But wait, I don’t know how to cook.” 

Claire couldn't stop herself from laughing at the genuine concern on the boy’s face. “I don't know how to cook either. Don’t flip, I’ll figure something out. Besides, the food is the least important part.” If they really had no clue they could always order food from a restaurant, put it on a plate, and call it a day. Although, Claire also enjoyed the thought of making Dean eat whatever horrendous meal the pair came up with. She had no doubt that Castiel would force him to pretend that it tasted good. 

“But there’s one problem —“ 

“What is it now?” Claire groaned, exasperated at the idea of answering more questions. 

“The problem is,” Jack continued as if Claire hadn’t interrupted, “that Castiel isn’t here. He’s been gone for days. How will we know when he’s coming back? What if he never comes back?” Jack suddenly looked worried. 

“Dude stop.” Claire said quickly. “Don’t get upset over nothing. Of course Cas is coming back. He loves the Winchesters way too much to not. Besides, you're still here. I don’t think he’d ever abandon you. Especially not because of some dumb fight with Dean.” 

“Yeah, I guess you’re right,” he relaxed with an embarrassed smile. “But still, I don’t know when he’s coming back. I don’t even know where he is. He could be busy, or he could be in heaven, or on a case. There’s no way of telling when he’ll be finished.” 

Claire thought about it for a moment, then she grinned wickedly. “I think I know how to make him come back. Give me your phone.” 

Jack looked at her oddly, but handed her the phone regardless. Claire opened it up and quickly typed out a message, she handed it back to the boy after she hit send. “There. I’m sure he’ll come home immediately.” 

Jack looked down at the phone with his face still scrunched. “Are you coming home soon? I miss you,” he read out loud. “Why did you put that?” 

Claire rolled her eyes, “What’s the big deal? It’s true, isn’t it?” 

“Of course I miss Cas, but I don’t want him to come home for me. He might be busy —“ 

“Bullshit,” Claire interrupted him. “It’s obvious why he left. He just confessed his love to his best friend and was rejected. He probably feels embarrassed, and now he’s avoiding Dean at all costs. Once he sees your text he’ll feel guilty and come back. He knows he’ll inevitably have to face Dean and besides, he’ll do anything for his little boy,” Claire pinched his cheek as she said it. Jack wrinkled his nose and swatted her hand away. “Trust me, it’ll work.”

Just then Jack’s phone rang out a _ding!_ The nephilim looked down at his phone with a pinched expression that quickly melted into a big grin. “It worked! He says he’s coming home soon.” 

Claire flipped her blonde hair behind her shoulder. “What did I tell you? Cas is a big softie, I knew it wouldn’t take much. Now come on,” Claire stood up and tugged on Jack’s sleeve. 

“Where are we going?” Jack asked, confused. “Wouldn’t it be better to work on the plan here? We don’t want Dean to find out.” 

“We’re having a sleepover, we have all night to do that. Besides, you dumbasses really need my help fixing things around here,” she said assertively. 

“Like what?” Jack asked, following her lead and standing up. 

“For one, did you know Sam has been moping around here for the past week because no one will talk to him,” Claire said thinking back to how eager he was to hear that she was coming over. Poor guy didn’t even know why everyone was suddenly upset and she couldn’t imagine Dean, Cas, or Jack telling him everything that happened. 

Jack suddenly looked guilty. “I didn’t think about that. I guess I have been pretty distant lately. He keeps inviting me to hang out with him and I always turn him down. I guess I didn’t realize that Dean was probably doing the same thing.” 

Claire rolled her eyes. “I swear you guys need to talk to each other more. Now come on,” she grabbed his shirt sleeve again and dragged him to the library. 

“Hey Sam!” Claire called out when she found Sam hunched over a book with his head in his hands. “When you’re done geeking out, do you want to watch a movie with us?” 

Sam looked up from his book startled, until his eyes landed on Jack and his whole face lit up. “Jack!” Sam exclaimed, ignoring Claire’s question. “H-how are you doing? I feel like I haven’t seen you in days.” 

“Yeah, sorry about that,” Jack winced. “I’ve been feeling kind of sad lately, but I’m better now. I talked to Claire about it and I think I feel okay.” 

“Yeah I kinda figure Claire had something to do with it,” Sam smiled. “I’m just glad to see that you’re okay. I was starting to get worried.” 

“So, are you in for the movie or are you just going to cry into your books all night?” Claire teased, going back to her question. 

“No, I’ve definitely had enough of this for today,” Sam said, while closing the book. “I think a movie night is exactly what I need.” 

“Can we invite Dean too?” Jack asked, with big sad eyes. Clearly, he was expecting Sam to tell him that Dean wouldn’t want to, which would no doubt lead to more guilt and self loathing for the nephilim. 

“Yeah, of course. I think I can convince him to join,” Sam said eagerly getting up from his chair. “I’ll go get him. You two can get started on the popcorn.” 

Claire followed Jack into the kitchen and watched him put a bag of popcorn into the microwave. She hopped on top of the counter and swung her legs absentmindedly. 

“Do you guys have any other snacks?” she asked. 

“Like what?” 

“You know, movie snacks. Like junk food.” 

Jack’s entire face lit up. “I know what we could have!” He walked over to a cabinet and pulled out a box. He dug his hand into it and pulled out a gold candy bar. He handed one to her with a childlike smile. 

Claire took it and raised an eyebrow. “Candy? Really?” 

Unfazed, Jack continued to grin excitedly. “Not just any candy. It’s nougat and chocolate, the best candy in the entire world!” The boy giddley took out a bar for himself. 

“Wow. I’m guessing you really like this stuff?” Claire said, still taken aback by just how happy Jack got over a bar of candy. 

“Yeah, I do,” Jack admitted with a slight blush. “I’d eat it all the time if I could. But, Sam and Dean made me promise to only eat it on special occasions or else they would stop buying it. I think you spending the night is special enough.” With that last thought, Jack decided to grab one more and tucked it away in his pocket. 

“You’re such a freak,” she teased, with no real bite behind her words. Jack must’ve understood because he merely smiled before turning back to the popcorn.

Sam found them once they were settled in the “Dean Cave” with a hesitant Dean trailing behind him.

“Dean!” Jack exclaimed once he caught sight of the eldest Winchester. “How are you?” Jack repeated the question that Sam had asked him earlier. 

Dean merely shrugged. “The same as I always am. Why wouldn’t I be? I’m glad to see you’re out of your room though. I was starting to miss you kid,” Dean said nonchalantly, as if nothing had happened. Jack and Claire exchanged a look that meant they were both thinking the same thing. That this was merely a front he put on for their sakes to cover up the fact that Dean was anything but fine. “Scoot over for me. Fuck yeah, popcorn,” Dean squeezed himself onto the couch next to Jack and helped himself to a big handful of popcorn. 

The rest of movie night went smoothly after that. The tension that had been in the air from the moment Claire walked into the Bunker was now gone. In its place was the usual homey atmosphere that she normally associated with the Winchesters home. Sam even convinced Dean to let Claire pick the movie since she was their guest. She decided to ignore Sam’s egging to play a “chick-flick” to annoy Dean even though she would normally be all for it. After hearing about his fight with Cas she would rather not upset him and potentially Jack. 

Claire decided on playing Deadpool since an action comedy from this decade seemed to be the best compromise. Apparently that was a good call because as the movie went on, any leftover tension disappeared and was replaced by their laughter. During the sex scenes Sam and Dean simultaneously scrambled to cover Jack’s eyes causing Claire to laugh so hard she nearly fell off the couch. Going by the way Jack hardly reacted, this was a normal movie night occurrence. 

Once it was time for them to all retire to their separate rooms, Sam pulled Claire to the side and thanked her. When Claire went to sleep that night she was pleased to find that her lump of guilt had finally gone away.

**Notes for the Chapter:**

> Yay Jack and Claire are friends again! I felt really bad after last time so I wanted to end this chapter on a much happier note! I hope you enjoyed it!


End file.
